Just be clear about your boundaries if the masseur starts to go past them; do it in a kind and friendly way and most will understand. It's less of a big deal than I suspect you're making it.
Pass. At least 10 (if not 15) years older than pics. Maybe the pics were him a very long time ago? Hard to tell. Perfectly nice massage but disappointing to say the least.
When he first hit the scene in NYC (fall 2016), I actually had a slightly more intimate experience with him; that being said, he does come across as "straight but open (with real limits)" if money is involved.