Been playing since the C64 days, and as time passes, tech and requirements move on as games develop more.
On that note, being able to affordably keep up is my main challenge. At times, when I play a more modern game with my present computer (it's quite due for an upgrade/update), I tend to worry about how much it can take before I have to worry about it. I always have some sort of system monitor up to keep track of at least the temperatures; before, during, and after playing a game. Being scared of modern games blowing up my computer (had my setup for nearly a decade by now) is my only rational fear with PC gaming nowadays (Main casualties: A hard drive, and a graphics card); and if I intend to join the VR bandwagon, my current machine won't keep up at all (Windows Vista 32-bit FTW!). Just as well, even with upgrading, I'm still nervous about having the latest Windows OS, mainly because certain features can't be toggled off for good, and other privacy issues I've heard about.
In the meantime, while I'm being a coward about hi-res gaming (for fear of losing my computer in the process), I've at least been having my fun staying within my era, where my machine more comfortably sits way above the requirement levels, and I don't hear my graphics card and the like. A quiet system is a healthy system. Unfortunately, all good things eventually come to an end, and even with playing it safe, I think my computer's near it's inevitable 'Time to Failure'. At least, according to my brother, it's at least 3 years overdue.
EDIT:
I suppose another issue I tend to have with upgrading is also the risk of losing reverse-compatibility as I upgrade. Like, as I upgrade my computer/parts, I lose some games I liked/been playing for awhile (Dyad being amongst the potential casualties (Unless, of course, I keep an old driver that is compatible with the game, which is at least a dozen versions old); since more modern cards/drivers work differently, and are no longer compatible). What doesn't help is that some of these games are still pretty recent, and have an unusually short shelf life, just by regular updating, either hardware or software/firmware-wise.