Before you agree to anything, my advice would be to find out if the roommate will make a quality tenant.

If you're a hands-on landlord on lower-quality properties, for example, 10 might be much harder.

And with that your going to learn more in 30 days than you could from 3 years on your own, you will get a great lease, you will have highest chances of getting top quality tenant, and you will have ultimate say on tenant acceptance. 

If you have a long standing work relationship with the handyman and the quality of work and communication is typically adequate, pay the him what he asks.  

Are you more comfortable having no debt at all (including properties), having 20+ properties with outstanding loans and HELOCs that fund other purchases, or somewhere in between those two? 

You might be able to find someone who does high-quality work, but they're likely expensive and might not have time anytime soon.

@Kendra CampbellBeing someone who owns mortgage notes and takes properties back all the time, finding quality updated bank owner properties is not common at all.

@Dan Wentworth, @Taylor L.Dan, Taylor has provided some very good initial steps to get you started with creating those relationships that will eventually bring you some quality off-market deal flow.I would like to reiterate the point that this is not an overnight process.

Most quality contractors I know have a lot of work and don't necessarily like dealing with investors because some, not all, are cheap and clueless.  

Or, a $500k house in the midwest or somewhere like Georgia will be nearly a mansion, and that high of quality of property isn't likely going to have a very high rentability factor because it's too nice... people in that arena will just buy.- what's the rentability factor and what kind of tenants will it attract?