Personally, I think its a combination of what several people are thinking.
Sadly, at this point Dylan has pretty well established himself as a user, IMM .I think he sees Jackson as a way to stay IG relevant, get to live in a big house for free and get to enjoy sex with a guy who turns him on (Jackson), without the entanglements of an actual relationship. Plus he can still get the sugar baby trips and perks too.
I think Jackson is in love with Dylan, and (like other guys we've all seen before) his feelings are blinding him to the realities of the situation. Not all that unusual for a horny/in love 20-something.