There's not really a "right" or "wrong" way to collect - its more a "right" or "wrong" way to collect for YOU! Sounds like you're still trying to figure out what that is. No problem there, nothing to be embarrassed about, and its not really awkward. Lots of people take awhile to figure out what they REALLY want to collect, some change their minds over and over again. It's not really a bad thing (unless you've got no self control and blow your budget out every month trying to support your "habit" or something like that ).
If you've got a bit of a
thing about having a "complete" set (or whatever it is) then you'll either have to get over that, or make that your goal -- to get a "complete" set.
My collection sounds a bit like yours, a little bit of everything - I've got nintendo (since NES), Ps1/Ps2/PSp, and 360/Xbox1. Some games I just have because they're fun - they're not really part of the collection I display on here because they're not a special "edition" or they're not displayed in any grand fashion -- I just got a bunch of 'em cuz I like them. It wasn't until this afternoon that I even took any pictures of these things (and only got through a few boxes at that) -- but some people just collect everything that catches their fancy (and it can be one of the most impressive collections!).
If budgeting is an issue - and you're looking to upgrade to "special editions" then you can always try trading/selling your standard copies for those, or just try picking them up cheap, there's always deals to be found for the patient.
I can't really help you with the crossing generation thing though -- you have to decide if there's any reason to keep your "last gen" stuff:
- do you like any of the games you have or that were available (that you don't yet have) enough to play them again or later?
- is it worth more to you to sell the generation now and invest in the "next gen" or will the collection you already have potentially be worth more $ down the road?
- it sounds like graphics etc. are important to you, is it more important to you that you have shiny new games to play in your collection or more important that you have a "big" or "complete" collection (these aren't always mutually exclusive, but collecting for ps3 generation is likely a lot cheaper on average than ps4 generation or going retro and collecting all the "rares" from ps1 generation for instance)
As others have said though, (and a motto I train others with in different areas of life) you'll burn yourself out trying to do everything perfect all the time and the results will be everything suffers for it (has less than stellar outcome), but if you focus all your energy/talents/resources on a few things, you can continually perform excellent. So yeah - find a goal, something you think you'll like to do - try it out, work at it, and be sure to share pics a long the way!