Great article!
*** LONG POST WITH LOTS OF BABBLING ***
I've been having this problem, or variations of this problem, for many years. I've tried hard to figure out why, and I've yet to fully grasp exactly what makes me keep trying when I don't enjoy myself.
In my own case, I've been passionately playing games since I was around 5-6 years old. My brother introduced me to the world of gaming, and though I couldn't understand much of anything back then, I was immersed all the same. Since I didn't speak a word of english, it was kinda hard to appreciate games for all that they were, but most were just little letters moving around on the screen in those days, anyway
Back then, games weren't released very often, and I'm sorry to say that we didn't have the means to acquire them legally, so we pirated our games back in those days.
This meant that whenever we DID get a hold of a game that intrigued us (and most did), we'd be much more willing to put up with whatever weaknesses it had. That patience and willingness to hold out has gradually faded, as time has passed and my tastes have grown more and more particular and limited.
I don't remember exactly when I first experienced the sensation that great games which could entertain me sufficiently, were becoming very rare. I think I was around 14-15 or so. I spent A LOT more time following development or news of upcoming releases than I did actually playing anything. Also, whenever great titles were released that I'd waited for, for months on end, I rarely played them as much as I had expected. Some games came out that SEVERELY disappointed me and left quite a few scars on my poor gaming soul.
I think the worst case of this was with Daggerfall. I don't think any game compares with the level of expectations I had of that game. I think I spent an entire summer doing VERY little except reading and dreaming about that release, and this is especially pathetic because I was around 18-19 years old back then. I wanted that game SO badly.
Anyway, it was released, and to give you some idea of how much I expected, I can reveal that I'd pulled the curtains and lit two candles for the experience. To partially redeem myself regarding my youthful piracy, I should mention that this was the overseas collector's edition (or whatever it was) with the 20$ strategy guide to boot
It took me at least a week to release that it was nothing but a pale shadow of what it should have been, and in the end I had to realise that I simply hated it.
Not only was it extremely buggy upon release, but so many of the features they'd promised were either left out entirely, or implemented in the weakest possible fashion. Ships, for instance, were nothing but empty rooms with a storage locker. In the previews they'd talked about ship-to-ship battles and what not.
In any case, such experiences left me extremely jaded, and after however many, I learned to remain extremely sceptical and reserved in terms of buying into hype. Interestingly enough, some of the very few games to get me excited since that time, have been both Morrowind and Oblivion, and they both managed to disappoint me quite a bit.
Oh, but where am I going with this... I know a have a point.
Oh yeah, that's it.
For me, it's the combination of being extremely picky AND extremely jaded that (at least partially) makes it SO hard to enjoy those few games that DO intrigue me. The picky part is responsible for there being so few of them, and the jaded part is making me pause everytime I sense I'm not being entertained sufficiently. I just don't want to be disappointed and I don't want to waste my time with games that don't fulfill my looong list of demands. However, and this is key, the reason I'm even bothering to try this, again and again, is because of those few truly wonderful experiences you CAN have with games (and yes, they still happen on VERY rare occasions).
So, it's a very circular thing, and it's really odd that I do this to myself, but that ever elusive great experience is what I'm chasing.
Also of note, is that many games tend to have vital bugs or problems that could POTENTIALLY be fixed and make the whole thing worthwhile and great. Often, I just start waiting for the inevitable mythical super patch, that's supposed to fix all the core issues. A good current example would be Gothic 3, which I enjoyed thoroughly until I understood just how buggy it really was, and lost multiple days of playing in the form of corrupt savegames.
All this means that I end up playing very few games, and those that I DO play, tend to be old classics, because I don't have any expectations of them whatsoever, beyond being what I remember them to be. Also, they tend to have very few serious bugs or omissions at this stage of being classics. I'm replaying Baldur's Gate (TuTu) right now, for instance.
Another significant factor is WoW.
Sadly, I'm spending way too much of my free time playing that timesink. Whenever I start playing something else, I start feeling an "obligation" to achieve something in WoW instead. It's like a job in that way, as I feel that I'm wasting time with an offline game, because somehow achievements mean more in a social setting. That's another big reason I can no longer become immersed in singleplayer titles as much as I used to.
Oh, woe is me.