In 2002 I intentionally purchased a two bedroom condo instead of a studio or one bedroom, because it made so much more financial sense to have a roommate to help with the payments.In 2005, while the condo market was still booming in Portland I sold the condo and invested the profits into four bedroom house.

It seems like kind of a pain to have this rotating cast of roommates.

He gave me their phone number and I talked to the guy, he said he's getting a plan in place and may have a place to go but his roommate might not and he still didn't have a for sure date of move out.

I don't see them doing much with regards to roommates.

Rent. you rent the house to a tenant or if you are going to be living there yourself maybe you find roommates or rent out other available units if it's a multi-unit property. 4.

He and his roommate got a very unpleasant surprise when they found a notice on their door informing them that the property was being sold at a sheriff's sale.

If you have friends/roommates/ significant others- are they onboard?

Do some research on "house hacking", buy a duplex, get a tenant on the other side to pay your mortgage and get a roommate if needed to help save more money. 

I'd be prepared to go up to $1100, but after that I just don't think its' worth.and before anybody asks, I will be having a roommate to pay his half, his name will be on the lease, and Ive known him for a while and will have him sign a seperate agreement with me becasue basically he'll just be paying me back for fronting the money.Speaking of which, can anybody get me a link for such an agreement?

At your age, buy a duplex and get roommates to pay.