Sorry to hear about your house. Hopefully your insurance company will compensate you sufficiently that you can recover.
As for your license info, I've generally found both Adobe and Apple to be quite helpful in this regard, it's worth giving them a call.
As for the endless cycles of upgrades, yes sometimes it pays to just "unplug" from the constant stream of news about imminent upgrades. I've had a personal policy of skipping every other Adobe CS upgrade because I don't upgrade my computer often enough to justify it. CS3 still works GREAT on my BlackBook and I'm sure CS5.5 will be a swell jump when I get my next computer. In the interim, by not upgrading to CS4 or CS5 (which wouldn't have worked as well on my older MacBook anyway), I saved myself at least $500.
I also tend to judge carefully whether to jump on the latest OS release or not. Snow Leopard worked out GREAT for this older machine, but the graphics system on it is such that if I still have it when Lion comes out, it might not be the best move (much as I would enjoy Lion). Might be best to just put off that upgrade until I buy the new machine (which will have it anyway).
It's sort of a process of learning to judge when the upgrades outstrip your machine's ability to take advantage of them.