Great post, chas. I'm a new Mac user (got my 15" MBP about 3 weeks ago), but have used Windows systems for as long as technology has been around. I teach technology and computer software (on Win only), so this was a big jump for me.
A few comments:
#2 and #3 -- programs: some software and programs you can't avoid installing. Well, yes, I suppose you could, but it makes things difficult. I'm talking specifically about the MS Office suite. A college kid relies on that. When a prof has a .docx or .xlsx document or requests a PowerPoint presentation -- it had better be able to be accessed or it better work when presented in class with
their software. Sometimes OpenOffice or other stuff just doesn't cut it. This is why students (and educators) are offered deep discounts to buy MS Office. Anyone who is a student or a teacher can purchase the latest version of Office for the Mac at well below the retail price. College bookstores are super-cheap ($33 for the 2011 version), but you need to have a college ID. Otherwise, students (and yes, that's K-12 kids) can get it for well under $100. Adobe remains pricey, but it still is much cheaper if you have some sort of educational connection. Agreed -- buy it. Pay the developer. The real deal is the best deal.
#6. Switch 101 is excellent, but so is
Mac 101. I used that site to navigate the interface before I even walked into the Apple store, and then I visited it twice as much afterward.
I also had people tell me not to sign up for One-to-One. I went ahead and disregarded their advice and paid the $99 for one year of unlimited private training sessions, because as I told them when I bought this, "I know enough to be dangerous." The few sessions I've been to have been superb. They got me going with Time Machine, helped me transfer my iTunes library seamlessly, and assisted me with installing an FTP client (since I maintain websites). I showed up with a list of what I wanted to learn that day and the assistant walked me through everything. So worth it.
That, and forums such as this, help me make an easy transition to the Mac, and I am loving it. When I walk into my classroom to teach on my Windows machines every day, I'm giggling because now I know there IS a better way!