I'm going to take this opportunity to say that Classic Mode was really not great and should not be relied upon. It usually didn't fail on me the few times I tried it, but it's conceptually messy and compatibility isn't perfect. I suspect Classic Mode was primarily targeted at home users who had non-critical things that they wanted to run without dual-booting; professional environments just stayed on OS 9 until they got native OS X versions of the software they depended on. Even within the past six months, I've seen a place of business with medical imaging software running in Mac OS 9 on a couple of workstations.
If you're moving house and have to bail on all your existing OS 9-bootable machines, I'd strongly suggest just picking up something OS 9-bootable (if space is a concern, perhaps a laptop to run in lid-closed mode?) after you get settled in where you're going. Ten years ago when PowerPC Macs had prices befitting new or slightly-used computers, it might be a legitimate concern to tough it out with Classic Mode in 10.4, but in 2012, when these Macs are being given away, it would be best to run OS 9 standalone.
As for Apple loving these "obstacles," yes, they always have, because it is good for them and their customers. Many common criticisms of WIndows stem from Microsoft's willingness to hamstring the operating system in various ways for the sake of allowing corporate IT departments to not upgrade or replace their software. Microsoft's bread and butter is in the business world, so it makes sense for them to do this. Apple has no such imperative, so they make their developers keep up, and it goes a long way towards explaining why their consumer products are generally better than everyone else's. Contriving bizarre scatological Wizard of Oz-derived fantasies does nothing to disprove this reality.
"Production" systems: Sun Ultra 24, ThinkPad X220, ThinkPad T23, SGI Origin 300, 2011 Mac Mini
Toys: MDD Power Mac G4, Quadra 840AV, various other SGI, Sun, Apple, etc.