Kind of depends. I can do it on my fire mage who’s not in amazing gear or anything. I think it comes down to how well you can play visions. Solo 5 masks should be a joke for you if you can boost someone in a 5 mask. So they definitely can be challenging, but so far I’ve never failed to boost someone through. It’s considerably harder to keep them alive if their cloak is low too, though. I prefer having them die at the first zone and AFK for the rest.
You also shouldn’t need any orbs for yourself in your normal runs. It definitely feels like a challenge above what the normal player is capable of. Depends on the spec too, boosting someone as a DH is easier than let’s say a ranged (except hunters). Also do note that there’s not room for a lot of mistakes if you’re boosting someone.