I don't want to make the switch to Mac OS X and then discover I've made a costly mistake. Here's how I'm planning to mitigate the risk.
The most obvious way to de-risk the switch to OS X is to try it out first. It's actually surprisingly cheap to do that.
After talking to some Mac friends and doing some research on the web (LowEndMac is a good starting place), I decided I'd buy a Macintosh G3 with at least a 400 MHz processor, 512Mb of RAM (apparently RAM makes a massive difference for OS X) and a 10Gb hard disk. This combination would run OS X well enough for me to give it a fair tryout.
I did some research on eBay to see what this type of system would cost. A basic iMac G3 400MHz with 64-256Mb of RAM and a 10Gb hard disk sells for just over AUD$300. To that I'd have to add roughly $200 for 512Mb RAM and $129 for an OS upgrade to OS X 10.3.
While doing this research I came across a G3 500MHz iMac with 640Mb of RAM, 20Gb hard disk and 10.3 already installed. It also included iLife'04, an external Iomega USB CD burner and an Epson 740 colour printer. Perfect! The buy-it-now price was only AUD$600, so I snapped it up.
I'll be running this iMac until almost the end of the year, when I'll be able to salary-sacrifice a new laptop. So I've got plenty of time to evaluate the platform and, if I'm happy, decide which Mac laptop to buy. At that time I should be able to sell the iMac package for at least $400, and recoup most of my investment. You've gotta love eBay - where else can you rent a computer for $200/year?
Since I've got lots of time for this evaluation, I'm breaking it down into small bite-sized chunks. By the end, I'll have looked at everything I do on a computer in day-to-day use, and I'll know whether I can still do all those things on a Mac. For each task, I'll try to evaluate whether I think OS X or Windows is better.
As I look at each task, I'll try to then only use the Mac for that task in the future. So by the end of the year I should be doing almost everything in the OS X environment, and my switch to a new Mac will be painless.
There'll be some commercial applications along the way (e.g. photo management software, VirtualPC, etc) that I probably won't buy, though, until I'm commited to fully switching to OS X. I'll download trial/demo versions of these products and defer the purchase decision until the end of the year.
So that's the plan - now on with the playing!