Tinkering is all well and good; and many times quite relaxing and enjoyable in it's own right.
If I've got time for a game, though, I'd rather be blasting Nazi's (or whatever floats your boat) than tinkering to get there. I still remember when I upgraded my video card to a Savage S4 and Half Life broke, requiring much tinkering, downloading, reconfiguring, rebooting, some more tweaking and finally a reboot to get back into the game. Then it isn't relaxing or fun; it's stopping me from the fun.
So a couple of bucks to GOG for their efforts to make thing run is a great investment, IMO. Plus it great to be able to get all the old titles again, long after the disks have been lost and the patches much harder to find...