We know that and assume this risk when committing to a tool. Of course, these efforts are very small when you end up using a synth solely for it's preset. But even then, you will probably need a certain longevity for those synths so that if you call up an old song after making some changes to your system, all the notes are still sounding as they should.
So, we know the usual pitfalls: changing your OS will mean incompatible software or even driver problem that may lead to an hardware change (Audio/MIDI interface). In theory you should get it all up and working within a few driver and software updates. But sometimes the company that sold you your software will just not support it anymore. Or worst: they went belly up!
Of course, you can take actions to protect you from these situations. The easiest way is to committing all the tracks to audio files, so that you lower your dependence to plugins for older songs. You can also keep an old setup that will always work with your older software. It's unlikely you'll take that path because your components can still fail and be hard to replace. It's quite a commitment for keeping track of old mixes. Usually, it's not worth it. Good practice is then to consider your old songs to be left for dead after a year. If not, you should update it so that it stay current with your setup.
But I'm realising more and more that on top of that, an obsolete software also means wasted knowledge. The thing is, the more powerful softwares gets, the more complicated they become. So, when you commit - often with a fair amount of cash - to a product, you'll usually want to become good at using it. You want to make it fly. It's at this point that you also also realise that software manufacturers assume you have no real life and that you are willing to spend hundreds of hours to learn there things.
And so you learn. And become good at it. You become an expert, knowing all the keyboard shortcuts, and tricks to get special envelopes quickly, or twist the bus setting to get the sidechain to work, etc. But all this knowledge is wasted with a software change.
My first sequencer was Hybrid Arts Edit Track. Didn't liked it much and latter went for Cubase 1 on Atari ST. When I switched to PC, I went for the natural choice: Cubase. When Cubase introduced the VST standard, I think it was with version 3, my computer wasn't up to this task. So I took the opportunity to take a look at the competition. And felt in love with Logic. So I went for Logic. Until version 5.51, moment at which time Apple announced that it took over Emagic and dumped the PC platform. Ok, so I decided to stick to Logic anyway. Well for a time. I mean, when you see ALL the other software making real-time audio sync to tempo, you start to feel left out in the cold. So I went to Acid 5. Then 6. Now 7. And the grass does look greener on the other side: Live. Or would it be back to Logic on Mac? Obviously I'm trying to stick to Acid.
That's without talking about all the abandonware I bought.
A great piece of software. I still love it and use it. But no updates for 5 years now. Obviously I must consider that I will have to do without it soon as it won't work soon (Windows 7 coming, Intel I7 CPU, etc).
Virsyn Tera 2
You could argue that Tera is still current. For my part I was very dissatisfied by the protection scheme used that made it a pain to install. So I was not too hot for a paid upgrade when version 3 came up. But on top of that it wasn't made available for download. WHAT??? I had to pay 99E + shipping + customs + taxes ... Forget it. So I end up with a software I paid close to 300$ for that will be abandonware in it's current form. Because Virsyn won't update version 2 is it's not compatible with future evolutions.
ReFX Trash, TBL ... eventually QuadraSID
Yep, bought those 7 years ago. Of the 3, only QuadraSID is still updated, but for how long? ReFX has an history of dropping their products when sales drops. I don't expect QuadraSID to live much longer.
SpinAudio RoomVerb M2
I thought I was getting a good deal. The company closed it's site about 2 years after I paid more than 100$ for this software. Dead.
Native Instruments Kompakt
Got it with Acid, and it was dropped by NI a little while after.
And that's without mentioning the hardware I had to drop because it wasn't compatible with my setup at one time or an other: Yamaha DSP Factory + ADB AX88, Opcode 8Port/SE, etc.
So what can I do about it? Is there a lesson to be had? Yes and no. I'm convinced you must commit to certain tools and learn them. I think there's only one exception so far to the pattern I described: CSOUND. Not even Pro Tools: at one time or an other you have to drop your old hardware to get the new version, etc. But of course on the software side, pro Tools is a steady one. But you can't beat CSOUND. It's been there forever, it's solid, for any platform and it can sound like anything you want. The learning curve is steep and the time investment is tremendous, so it's not for everyone.
I'm not going 100% CSOUND, it's too much for me. But I think you must consider it if you want to avoid the above frustration.
The other shift I made was to see my recording session as a live performance. What I'm recording is my performance. Commit every track to audio, and that's it. But it's hard to make that shift. Still working on it.
How do you cope with obsolescence?