I don't know how relevant this comment is, but here goes...
I started out with p&s until I felt they could not get the quality of picture (and camera since I seemed to break them) I wanted. So, I got a Canon Rebel K2 film camera and really liked it. The quality was way better and it peeked some real interest for me. I started using manual controls, and got even more interested.
I decided to get a DSLR and the prices were disappointing to say the least, (I can be a tight wad) but I thought with the interest and motivation I had, I would want a good one. So, I researched and checked out a few Canons and boiled it down to the Xti, Xsi. Until I saw I could get a 30D (body only) at the same price as an Xsi. I bought it and love it. I think my learning curve increased by getting the DSLR since I can shoot and see the results quicker.
Bottom line for me is trusting my interest and motivation to learn it. I've picked up a lot of little hobbys and gadgets along the way that have been abandoned somewhere. So, when I decided to get the 30D, I made sure I was willing to go the distance... now I just need more time off from work
edited: Oh, yea, as far as ease of use: As long as you read your manual and keep it handy, its real easy! My 30D is not as 'user friendly' as I'd like, but once you learn the controls, its no problem. Search or buy a photography book (search TPF for which ones) and go shoot some pics.