I must say that I kinda had to go through this same thing. My brother started living with me at a time when his life was in great transition....so many of the things that you described were quite familure.

I'm not sure how your household finances are set up, but for my situation, I pretty much pay all the bills. He pays his portion of the rent, but the "house" bills are mine. As such, I used that excuse as a "I'm already giving you money. You get no cash from me." Thankfully....that's changed over the years.

But, as in your situation, there was crap everywhere. There would be shoes....clothing....whatever all over the place. For my own sanity, I had to do something about it. I'm not compulsively clean or anything like that...but it was past a point that I was comfortable with. As such, I would bundle all his crap up, and just toss it into his room. It was his room....he got to deal with it.

When it came to the common areas (living room/kitchen)...I would take care of those....because I couldn't live like that. And I *refused* to clean his bathroom. Ultimately, the shame of asking guests to use my bathroom as opposed to his guilted him into cleaning it. And then when we got a maid, I specifically told her to not clean his room/bathroom until he contributed financially to paying for her services. When the rest of the apartment was *awsomely* clean, he liked it, and was eager to join in.

I'm not sure if any of this will work in your situation. I know my brother well, so I knew it would work. We've lived together going on 7 years or so...and it is working out well. I refuse to have another roomate (unless financial stuff gets unbearable).

Good Luck.
~Jeordam