This issue is more acute for musicians and media artists than it is for most people. The problem is a stack of dependencies. We open our document in a DAW application. Usually, there are a number of plug-ins and virtual instruments that we use in our documents. Some of these applications and plug ins may require additional copy protection software to operate. The application itself requires a certain version of operating system. That operating system only operates on a certain range of computers. The DAW software may use audio hardware. The hardware requires drivers that are dependent on the OS version and computer hardware, etc, etc...
Each of these dependancies have their own life span and release schedule and they're all interrelated. Update your computer or operating system and you may be surprised that some upper functionality get depreciated. In my lifetime, I've seen the transition from MFS to HFS. From the first Mac OS to OS7 to OS9 to OSX. From serial and ADB to USB. From floppy drives to nothing. From the Apple External Drive Port to SCSI to Firewire. From 68K to PPC to Intel. Each one of these transitions demanded changes to everything running on top and in a lot of cases, some software didn't survive the transition.
Some changes are self-drected. At one point, I was using Performer, but got really interested in Max and the people around me were using Vision, so I moved to a total Opcode system with a Studio 4 interface. I synced this to a couple of ADATs. Then I moved to Pro Tools hardware with Studio Vision. Needless to say, accessing those Studio Vision documents today is difficult.
It is enough work to get a complete production system running, but near impossible to maintain a system with 100% backwards compatibility.

But really, the context of this post came from thinking about virtual instruments versus hardware. If you have MIDI data, you can play it to a virtual instrument, or you can play it to hardware. Now, forward 15 years. You can take the hardware out of the closet, play the MIDI data to it and it works. If you're using a virtual instrument. Well. Good luck.
So, what to do?
First of all, you need to render everything you have as a broadcast wave file when you archive a project. This includes virtual instruments and tracks with effects. Sounds pretty simple, but in practice it is more complicated. And a supreme pain. If you're done with a project, you just grit your teeth and do it. But, what about projects in development and those that never get finished? At what point do you shift into archival mode?
Another strategy is to limit your dependence on third party plug-ins and virtual instruments. This, obviously, sucks.
I've had some luck with accessing data with virtualization. Obviously, this isn't going to work on hybrid hardware/softtware systems. That is, unless someone comes up with a virtual ProTools III emulator, for example.
I have friends that archive their computer hardware. Sort of like freezing it in a preserved state. This is a good option if you have the space the store the equipment, and if you're planning a major shift in process, like switching DAWs. Most people I know sell off their old gear when they're done with it, though.
What are your strategies? Do you have any horror stories?






