If he moves out and leaves damage to the property, a fresh coat of paint won't help you too much.Personally, I'd treat "Joe the Painter" completely independently from "Joe the Tenant".  

Rent out your nice, freshly remodeled house for $1400. 

BP is cool and fun to ask questions but this is not nearly enough to learn it all.

Sounds like a fun situation.

It's all fun!

It's been fun :)As far as buying a home vs the investment properties, here's my personal recommendation!

Anywhere from East Falls to the far edges of Manayunk will give you an affordable place to live (and have fun) as a young professional and still be able to ride into work or take the train when the weather gets bad.

The closer you can get to the ski resorts, the better, or in the heart of downtown.Have fun!

It was FUN..

Look at the managers for both sectors; look at the amount of work that you will be doing- pick the option that allows you to learn as much as possible and develop your skills as a real estate professional (the job/manager that is fun might not be the best for you to grow).