My buying habits have been all over the place. I still can't say for sure that I've settled into a groove, and I know for a fact that I still fall victim to the hype trap.
Seems that we're in a boom period now, i feel like I've seen this all before with the trading card and comics markets (not to mention beanie babies LOL). Variants, printing gimmicks, it's nothing new. If you feel like you want to make a long term investment, I would be very wary of buying pop culture prints. The current heavy hitters will likely still hold their value if not continue to appreciate, but that ship has sailed. There won't be another Moss or Stout Star Wars set. Print runs have soared, even the best new prints will never reach a level of scarcity that leads to the kind of demand that really drives prices up.
I ran out of wall space a ways back, so if I buy something to hang I know it will need to displace something else. But then again I also bought a 10 drawer flat file, so I know I can store everything indefinitely.
So what do I buy these days? All the Horkey. I just love the dude's work. All the fat birds. Random crap that catches my eye. Prints that fit in my 18x24 itoya portfolios so I can see them without having to dig through a pile in a flat file drawer. Sometimes I buy prints I don't like from artists that I do like just to help support them and their work.