Pro C# 2008 and the .NET 3.5 Platform (Windows.Net)
C# has a free implementation in Linux under the Mono project, and it arguably is a very marketable skill unless you're completely anti-Microsoft.
My favorite C# book is Pro C# 2008 and the .NET 3.5 Platform, Fourth Edition.
If you're really want exotic, F# is an OCaml style language that runs on the .NET platform and mono, and is getting a lot of attention these days.
Books for F#:
Apress's Pro C# is an excellent book that covers both the C# language and much of the .NET libraries.
This is really a simple question... with a complex answer.
You are asking: How can I plan a complicated software project?
Know your environment (which you sound like you do):
Know software engineering:
Know your language/developing environment:
If you are nervous about starting, then I would create a simple functional prototype. Start with visualizing the project in something like Balsamiq Mockups, so that you can see how each piece of the puzzle will come together.
If you take a few days of researching software engineering methods, you will save yourself hours and hours of headaches. Start with good practices gifted to us from those alpha geeks who've already done what you're trying to do.