MoP shadow priest and balance druid.
MoP discipline priest. I could sometimes outDPS dps players in SOO and be first in healing done 
Back then i loved the need to track your procs, track if your trinket is up or your head gem did proc. It was a big deal and made the difference between good dot DPS and kids.
Legion fire and arcane mage. Arcane could burst 4-5x harder on encounter start then any other class. It was epic. And fire was very strong and solid spec. Now its 0crit garbage.
Legion priest had issues but overall was one of my best experiences. Hitting 65 voidform stack i feelt like a god. + the army of shadowy apparitions 
Dk was best in wod by far. Espcially unholy and blood.
And then legion had to ruin them >.>
It just flowed so well together. You had alot of options and unique skills/stuff.
That could make you shine as better player
And had various runes still the most unique rescource system we had.
(Will edit more in once i get back home to my pc)
Mop wod demonology warlock…and ofc 2handed frost dk before they removed it in legion.
I loved my arcane mage in Legion. 
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I skipped MoP, but looking at the rest of the expansions and vanilla, my most loved times for the various specs were WotLK for balance and the third part of Legion for feral. Cat played really well after Antorus came out. I had a ton of fun catting around, and was crushed when the BFA pre-patch came out and my kitty felt so cumbersome to play. Resto worked well for me in all eras of the game, except vanilla and Cataclysm. Healing in Cataclysm was a real turn-off for me.
I am actually starting to enjoy both feral and balance in BFA now, too. The essences and better gear levels helped both specs a lot. I struggled enjoying moonkin earlier in BFA, even though I played it. But by now it flows much better, and feral is a much improved experience also. Not Legion-level of enjoyable, but it’s more fun again.
TBC, no question.
Classes were still unique back then but all had a reason to exist.
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For me, priest was fun in every expansion up to Legion. Sometimes more fun that other times, and if I had to pick a single one to talk about, it will be Mists, because that’s just pre-pruning and I feel not just my class but classes in general were more appealing then, and the expansion’s class design is modern enough to not feel like going back in time too much.
- rotation isnt exactly a thing for healers, so I won’t talk that much about it. However, the atonement mechanic of MoP felt very much in place in pve and not a gimmick, there were various cooldowns to use for almost any situation, the playstyle felt dynamic, no button press felt unsatisfying (on the contrary, pressing something like Divine Star from the right angle and distance felt godlike), and playing it in pve tended to be less stressful and more enjoyful. In pvp, there was a ton of utility for every class, including priest, though I would say that after S2 when the priest-feral synergy wasn’t as great as before, perhaps priest was a bit hindered by the overwhelming amounts of CC everyone had, and towards the end the only really great setup for priests was beastcleave because of the access to shaman anti-cc, whereas in traditional priest comps we were getting replaced by other healers (RMD in rogue-mage, and so on), a trend that continues to this day.
- the utility, especially in pve, was generally in very well times cooldowns. There was an answer with a shorter cooldown to raidwide damage in the form of spirit shells, there was power word: barrier, priest was the healer that actually did real damage in pve which was an upside, things like spectral guise were very useful in things like challenge mode dungeons, there were emergency tools like power word shield being massive. 3 types of CC were available to priest as well (4 when symbiosed by a druid).
- in PvE, MoP is what I would call the dream expansion. It was that one time when I absolutely liked doing PvE for the sake of PvE, something that doesn’t normally happen to me. Usually, when I do PvE it’s nothing more than a passtime or a means to an end, but in MoP I’d say that my priest, as well as my favorite alts rogue and hunter were tremendously fun to play, as were other classes that I made - warlock, dk. In PvP, I think MoP was possibly one of the best expansions, but for me personally it had two downsides: the amount of CC was over the top, especially the instant CC, and since healers are the prime target for said CC, I can say that this dampened my enjoyment of the expansion some. The second problem was that after the first two seasons, the meta shifted to become dominated by wizards, and I personally enjoy the game more when melee are good - the game is more alert, it is more suited to my class in my opinion, and I just find it generally more fun to play against melees than wizardcleaves.
- class fantasy was just fine. It was what priest had been from the start - a healer with pretty good non-HoT heals and with powerful shields, as disc the emphasis on shielding was very high and I enjoyed that a lot (power word: shield was the reason why I rolled a priest back in Vanilla to begin with), and I feel that being the offensive healer has always been an important part of the priest toolkit. At the same time, I absolutely loved rogues and hunters, especially combat and subtlety rogue and especially survival hunter, which felt just right as an agile ranged combat class, as little as possible similar to a caster. After MoP, I was constantly disappointed by the changed done to the hunter class, to such extent I haven’t played my hunter alt afterwards in any meaningful content.
Counterpoints to my class in BfA:
- priest design changed massively from the original strengths, which were essentially better dispels than other healers, better damage than other healers and heavy emphasis on shields;
- I dislike every new mechanic that healing priests got. I think the insanity mechanic for shadow might be okay, but I don’t like playing shadow so I don’t much care for that;
- I dislike how discipline is a one trick pony for raiding now, with some bandaids slapped on top to make it barely workable in PvP and dungeons;
- I dislike how priest is no longer the healer with the highest damage potential;
- priest dispels are nothing special anymore;
- the decision to nerf focused will (the passive that provided 30% damage reduction) was a disastrous one. Priest is a healer with zero mobility, when it’s not tanky it simply cannot survive.
- too many cool abilities got removed or nerfed to unspectacular levels - spectral guise removed, void tendrils removed, angelic feathers nerfed to half their MoP value and double their cooldown, psychic scream which always had a cooldown of 30 seconds now requires a talent to do that, power word: shield is a joke now, divine star is a joke now, shadow word: death removed, prayer of mending made holy only, renew made holy only, utility had cooldowns increased across the board or outright removed like spirit shells, inner fire made a pvp talent only for holy, and the list can go on. The only addition that I thought was cool since the start of Legion was the pvp talent Premonition, and even that got nerfed into oblivion in the 8.2 patch, because some stupid essence turned it into a pve ability.
- healing priest viability in content is at an all-time low - while it’s good in raiding, the latest AWC cup didn’t have a single GAME in which a priest was used (any spec, even shadow), showcasing how barebones the priest class really is, with no worthwhile utility besides broken damage and underpowered anything else to bring to the table. This is not even a trend that is recent, in fact since the start of Legion, priests are almost never used as healers in high end PvP teams, which all seem to prefer just about anything else. Shamans seem to have the most trouble lately aside from priests, but the issues shamans and priests face are of a different nature: while shamans have a pretty good toolkit (not resto druid god tier level, still pretty good), while their numbers seem to be utterly screwed lately, whereas priests have a class design issue to begin with, where only overpowered numbers sometimes barely keep them afloat. MDI teams never use anything but resto druids and back in Legion used holy paladins and resto druids, which once again showcases how priests lost even the traditional more offensive healer style we had in favor of druids and paladins, no longer having anything worthwhile to bring to the table.
Tl;dr: MoP would be the benchmark expansion of modern WoW for when classes were good. Pretty much everything I played then was fun to play. BfA too barebones, too many deviations from the original class idea. Start from MoP design, maybe a bit of instant CC pruning would be ok but the rest was top notch enjoyable for me.
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Cata was the pinnacle of class design and gameplay. It had its flaws but was still the peak. After that its been chaos.
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WotLK as my hunter. Not because of rotation or anything like that I can barely remember those I’m too old and forget easily. The reason I felt like Wrath was the most fun I last had with my hunter is because I still felt useful like I brought something extra being a hunter as we were still required to kyte back then I think in icecrown (like I say the memory is hazy). That isn’t to say I haven’t enjoyed the later expansions legion was great and although its an unpopular view amongst hunters I actually enjoy survival (much better in legion).
One extra note from a hunters point of view though I do miss Pets being different and no I know we have 3 types I just think it was more fun having much more diversity in pets but I’ve never been a min/maxer so never worried about having the best.
I enjoyed being a combat rogue, I never really enjoyed being a wanna-be pirate. Outlaw is failed because it forces one into a theme, instead of a spec.
That said I enjoyed my rogue most in WotLK (once it was leveled up and raiding, leveling has been nightmare) because of free energy, and didn’t need so much haste as we do, and in MoP for all the utility back then. Example of “smoke bomb”, so I could mitigate for the raid, or just vanish and mass ress every one when wiping. Made me feel useful.
I enjoyed my discipline priest most in WotLK. I loved shielding everyone, and waiting for that crit to make my Divine Aegis pop. In fact I had leveled my discipline priest just because I loved so much the look of divine Aegis, it doesn’t even exist anymore RIP. Thanks Blizz.
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WotLK Fire Mages was absolute blast (ba dum tss).
But really, they had the best dps flow and dynamics. With high crit % it was so fun, smooth and engaging spec. You felt that every percent of crit matters. BIG numbers of pyro, and if you’ve played in that spec enough - you start to feel when you can pop fire blast for crit and blow a pack of your hot streak combos.
It was awesome, truly awesome. I miss it.
Warlock in mop because it had tons of instant cast spells, like fel flame, that could be used on the move and it had slows and cc to deal with melee. Nowadays it’s just a hardcasting punching bag.
Bfa is the worst warlock incarnation I have ever tried to play. In Legion at least it had good survivability with drain soul, now that was replaced by a hardcasting shadoebolt lmao. RIP my lock.
Plus meta looked cool af.
Blood DK dps at the start of Wotlk in PvP.
Shaman during Vanilla-Wotlk.
Hunter in Wotlk
Priest in Wotlk
Druid in TBC and Legion
Rogue in Cata
Paladin in Legion
Warrior on Wotlk and MoP
Warlock during the end of Wotlk, with the old school hand of gul’dan.
Mage any expansion pre-Wod.
Monk and DH I never reached max lvl with
I’m so happy to find someone else who thinks this too! I miss shadow orbs so much… Used to love shadow priest but can’t play it at all now.
I only started in WoD but have changed mains each expansion due to the changes to classes. In WoD I mained shadow priest and loved it - I felt like it flowed well, you could get health back from spending shadow orbs so didn’t need to disrupt your rotation to heal. The changes to insanity mean I just stare at the bar and frantically mash my buttons waiting for something to be off cool down. Not fun for a player with little peripheral vision!
In Legion I mained affliction warlock and loved it. Again, the rotation felt fluid and wasn’t over complicated. The artifact effects worked really well with it. I felt powerful and invincible and actually useful in group content. BfA changes made it feel slow and clunky, with far less survivability and much more reliance of tank pets which die all the time…
Now in BfA I main resto druid. I miss some of the effects from Legion, such as being able to move while casting tranquility. I miss healing touch but I’ve adapted now.
My favourite class and spec to play now is disc priest. I didn’t play it in any earlier expansions so no idea how it compares to past iterations. But it’s the one spec I really love at the moment, even though there’s a lot I still need to learn and improve so I can play it better.
Holy Priest - WOTLK
Arcane Mage - Cataclysm/WOTLK
Destruction Warlock - MOP/WOTLK
Holy Paladin - WOTLK
Hunter - (Survival) was Cata, BM was MoP and MM was WOTLK and Legion.
I did prefer playing my Hunter during Cata though.
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Classic = Warrior
TBC = Pala
WOTLK= Mage
Cata= Hunter
MoP = Lock
WoD= Rogue
Legion= Druid
BFA= Druid and hunter.
Legion was the prime for arms in my eyes.
I’ve played Priest (all specs) since forever.
I’ve enjoyed it in each and every expansion. Don’t really have a particular favorite. The class is always super fun to play in the beginning when you get to try out all the new stuff, and then by the end of the expansion it starts to feel boring.
I appreciate the fact that the spec changes with each expansion - I enjoy that the most.
I think I’d start to find the class (and the specs) boring if they remained the same for too long.
If it’s new, it’s fun. Change for the sake of change is 
for me. And the more change, the better.
I always pray that my class is on Blizzard’s to-do list for a major overhaul and re-design, even if I don’t think there’s anything really wrong with it. I just want lots of changes. 
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Protection paladin in Wod. The biggest thing that legion brough is prunning big time. We lost hpower and got our damage values adjusted,lost cool set interactions lost more of our utilitY(clemency) lost hand of purity/salvation. Like after wod i just realized that even if i play perfectly my paladin the damage/survivability is barely noticeable. BFA somehow has made the gap between bad prots and good prots bigger(which i am grateful for) but the gap between a mediocre paladin and a really good one barely exist. We have no resource seriously we just have cooldowns i’ts the most boring shi* ever also it got even worse with the gcd strapped on top in BFA when we are one of the few remaining class that has to do 5 sec openers where we don’t do any direct damage(consac>(insert font if you have)>wings>Seraphim> now you are good to go).The prunning in Legion and gcd in BFA literally killed the class. Also rip captain america set from HFC at least legion tried to provide more avenger shields procs but legion killed the target selection to 3 for avenger shield since we had legendaries to buff it up. Where is the re-vert of prune now? There are no more tyelcas i want my avenger shield to bounce back to 5 targets and i also want it to be my highest damage abbility,with the damage shift avenger shield just feels bad to use… That’s like the coolest spell from the class it’s like making chaos bolt hit less than imolate completly bullshi*.
I love they removed holypower it should never have been a thing in Cata to start with combo point system for all classes has to stop be removed in my view.