- Given that your computer is free, the cost of a Mac over a PC is the cost of a copy of Windows to enable Boot Camp to run all your PC software. After that, you have the same ability to run your old software that you ever had. Plus the ability to upgrade to VMware to run OSX simultaneously with Windows if you find that you wanna.
- If you do elect to run Windows under VMware, you boot from a clean install of Windows every time. Making your Windows system more reliable (so I am assured, I've never tried it).
- Time Machine is a reassuring feature of Leopard which I have provided with an external hard drive.
- Apple sends software updates to keep ahead of software vulnerabilities before they are exploited, and they produce upgrades to OSX that are real improvements and not change for the sake of change.
- You mentioned handing computers down in the family; I recently handed down a five-year-old G4 Mac to my daughter, and she is delighted. (in that time it did have a hard drive failure, and for Christmas my son upgraded the RAM, otherwise no maintenance besides getting a wireless mouse). Macs tend to have good resale value. I made a mistake not upgrading to Tiger when it came out, and as a result I ended up springing for a new iMac when Leopard wanted a faster processor than I had (but OSX isn't noted for running slower with each upgrade). Otherwise I'd still have the same box, and been happy.
Not by default. But a good tactic is to do an initial Windows install with all the updates to a solid starting point, then copy the VM file or use Fusion's snapshot feature. For this stage I'd suggest copying since you might later want to build a machine for a different function and this gives you the pristine OS to start with, saving you hours.
Then install all of your apps and configure them as you like, then snapshot again. Thus you always have two solid base points you can go back to.