One to One worth it for an iMac

You should be fine by yourself. If you run into any trouble, there are some very smart/knowledgeable users here that are willing to help.

I would manually move my files over if I were you. OS X already has directories dedicated to music, videos, documents, photos, etc. to make it easy - you can place the files wherever you'd like, though, just like on Windows.

 

They will happily transfer your files for you at the store if that's where you buy it, but I don't know for sure if they'll do that if you buy one online.

You don't need the One-to-one because like Stooby said, there are plenty of people on here that know what they're doing. I was a middle of the road computer guy as well and had no trouble learning the OS X way of doing things. The learning curve going to a Mac is not as steep as going from a Mac(in my opinion).

And I would always recommend Apple Care but you could also wait a couple of months since you get phone support for three months and service for a year automatically.

 

End user recommends 1 to 1

On my third Mac (MBA) after 5 years with Apple computers. First time enrolling in 1 to 1. Great addition. Essential? No. Helpful? Absolutely. And you are being coached on your own machine. Two thumbs up as far as I am concerned.

 

I reckon you learn more by playing around and digging up your own information on the forums.

 

I've done it both ways, on my own and letting Apple do it for me. I prefer the latter. However, it might be easier to do on my own now than it was however many years back it was that I did it before. I'm thinking about letting Apple do it for me next time, because I'll be jumping from Leopard to Mountain Lion.

 

You don't have to bring your own iMac in for One to One. They have special training Macs (loaded with all sorts of photos, music, etc) that you can use. Also, you'll get access to the One to One website, which has a crap ton of excellent training videos that you can follow along with from home, as well a way for you to keep track of what you've already learned, what you want to learn next, and a place to jot down questions so the next time you're in the store for a session, you won't go brain-dead when you have a "live" person in front of you to answer anything.

I like One to One because it doesn't just cover the new Apple product you bought .. it can be used to learn any Apple hardware/software, including stuff you don't own. Say you think you've outgrown the capabilities of iMovie, but you're not sure if shelling out $300 for Final Cut is a good idea. Schedule yourself a One to One session on Final Cut. You'll get to play with it/learn from an employee that knows it.

I don't think learning the basics of a Mac is hard. There are a ton of online resources you can google around for, or ask questions on forums like here. But I do think One to One really can help you get the most out of your Mac, especially with the creative iLife applications.

It's been a year or two since I worked at an Apple Retail store. Since then, they've launched "Personal Setup", which is free to everyone, where they help you unbox your new Apple product and get the basics setup (i.e. create a user account, etc).

Data Transfer was never a free service when I worked there -- it was part of One to One. Not sure if that's still the same way now, but since it takes literally hours to do, and employees do it in the Back of House (so the computers can be safely left unattended during the long file copy), I doubt it's free.

You can look up your local stores phone number and give them a call to find out for sure.
http://www.apple.com/retail