I have been unable to sell my house so I ended up renting it starting in Feb. 2008. I have a friend who agreed to handle any maintenance problems and bill me for the repairs he does for a monthly fee, since I don't live in the state anymore. Do I need to send him a 1099-MISC or could he just send me a bill for services rendered? The repairs in all cost around $1900 including parts and the fee ended up being $825 for the year.

Yes, a Form 1099-MISC IS required unless he is working as a corporation.

And, if you have not already submitted the form under a Form 1096, you are officially LATE and may be subject to a fine.