The other option is bit-rot and some form of DRM (the only way to enforce subscription) which would make playing the games an impossibility, even with emulators. It's clear to me the non-subscription/non-DRM option is the better one: even with subscriptions, no publisher will last forever.
I've also got a desktop with tech mostly circa 2000. It's got DOS and Windows 98 on it. Among my collection, I haven't found anything that I can't get to run.
The hole that I see is during the time shortly after Dosbox's release when its compatibility with software would've been low and before they optimized for speed. It'd be closed up somewhat if we could send the current Dosbox source code back to 2002 ;-)
Because without it, you could be 100% sure the developers won't be updating them.
Now, lots of games from the late 90's, early 2000's don't work anymore on modern Windows versions. And DOSbox isn't powerful enough to run them.
What you do now?
Me, Personally? I have a Pentium 3 desktop running Windows 98, with a GeForce 4 video card. It's also got a Sound Blaster 16 video card. I consider it my machine to cover an era from the 80s to about 2002, when I can't run the software anywhere else. Actually, I mentioned that machine in my last post.
An example piece of software: Rayman 2. I had trouble running it under Windows XP, 7, and Wine in Linux. It won't run in a VM because it requires (I think) DirectX 7 and hardware acceleration. It's a flawed example, though: it's had a few re-releases, including a compatibility fix by GOG for modern Windows versions.
A more recent example: Vampire: The Masquerade - Bloodlines. It'll run on more recent versions of Windows, but has trouble with having over 2GB of RAM (or was it 4?) available. Some lovely group logged the system calls and developed a binary patch to allow it to run on modern systems. This illustrates another option: banding together as a community and doing what the publisher won't (or can't).
A lot of the posts in this thread (including yours) seem to elevate convenience to the level of a technical requirement. At some high-90s percentage of coverage, that isn't a problem for old software. Every once in a while though, you have to do the inconvenient thing.