I'm probably cheating myself here, because what I want to do should be possible right now. If 'money was no concern' I'd finally lose all arguments against
.. learning system level C (embedded kernel/driver stuff)
.. commit full-time on open-source projects that I love
What I have found helps me get over these "I know what I SHOULD do..." humps? If I pick up a book or find a good source of information on the subject and start reading it, I find that it lowers the barrier to entry for me just enough and starts filling my head with enough good ideas that I have to move forward.
You might pick up a good Kernel beginners book (do you know C? If not, start there.) and just start reading it... thumb through it... start seeing some of the API calls and comitting them to memory so the next time you see them you think "Oh yea, I remember that from Chapter 1..."
Don't worry about coding, which IDE to use, which build system to use, installing Ubuntu on your laptop or moving in with Linus... just get that book and start reading before you go to bed at night.
It'll either break down the barrier to entry for you, or make you realize it isn't what you thought and you can focus on something else.
Absolute worse case scenario? You learn a few cool tricks and put the book on your shelf to collect dust. No biggie.
I spent a considerable portion of my teenage years wasting away in front of books like Windows Internals in the hopes that I would be slightly better at writing rootkits and exploits than the next guy. It's a pretty fulfilling skill and meeting someone with real (I stress real) deep kernel knowledge basically never happens, which can give you a reputation for solving the unsolvable, which is both positive and negative. As you may have surmised however, it's effectively commercially useless to have reverse engineering, assembly or kernel mode driver development skills -- That considered, I'd highly recommend you give it a shot, 'Understanding the Linux Kernel' and 'Windows Internals' are some of my favorite technical books. If you have only a rudimentary understanding of memory paging and assembly, I'd recommend 'Reversing: The Art of Reverse Engineering' and 'The art of exploitation' both published by No Starch (Which also publishes two highly recommended, but certainly not my favorite - "Designing BSD Rootkits" and "Art of Assembly").
.. learning system level C (embedded kernel/driver stuff)
.. commit full-time on open-source projects that I love
I know, I know.. I should just start!