I get so tired of this "all or nothing" type of thinking. $50,000 to switch to Mac OS X? C'mon!
Using your own numbers, how about $200 for Jaguar and a RAM upgrade. Load OS X on your computer and take advantage of the tools and applications that come bundled free. Get to know it.
You can always boot back into 9 when you need to use the other apps that you're not ready to purchase for OS X yet. I still have an iMac that's all OS 9, and will probably remain so for some time. But I was able to switch my laptop to OS X, and I'm having a ball with it.
I can't believe the lack of creativity I'm reading here.