Classic isn’t going anywhere. Unlike in retial, all this content that you experience will stay relevant.
Me and my wife started during the launch night and we aren’t even 40 yet. Lot of players out there who take it slowly. Just game on and enjoy. 
No, but choose carefully your server. Check low lvl aeras, if they are full , go ahead
Classic has no AP grind or other such things you need to upkeep so never too late!
You’ll probably level side by side a few alts of peeps who already have a char at 60
If people have their gear it means that you can get all gear they don’t need = If people are bis geared, you can easily get bis gear without competition.
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