Like you stated, this is your very first venture into Linux. And while sometimes diving into the deep end is the best way to truly learn somethings, based on your list this will not be happening.
One of biggest things on your list that stands out is your requirement to "keep in your old ways" while at the same time trying something new. Those are mutually exclusive. The best way to reconcile these differences is by a virtual machine, and once you have your toes wet and feel comfortable being in the water, you can leave the kiddie pool and swim in the regular pool by doing a native install.
The most helpful advice I can give you on your Linux venture: Don't expect everything to work, don't expect to be able to use the same software in the same way you're used to, and read. Read before you click, read before you type, read before you read. And learn how to (use) google.
P.S. this post is not meant in anyway to sound anything less than helpful. And while there is a lot of helpful people in the Linux/Open source community, there are just as many jerks who expect you to know everything. to counter this: do as much googleing and footwork on your own before asking a question (to show you tried to solve it yourself) and provide as much detail as possible.
Edited by stumped - 2/21/13 at 4:19pm