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.  

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.

So you would be at a total of just under $300k to maybe $350k (to be conservative) Where in Pasadena, assuming a great flow and design that is cohesive and aesthetically pleasing would give you a value of about $550 to $700 per sq ft : at $600 per sq ft value X 1000 square feet: that would be an added value of $600k (depending on neighborhood and comparable homes )Spend $350k to get a value of almost double: $600k Take timing into account, holding costs, utilities and think if you will want to live in the property ?

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?

We had briefly considered trying to see if the home could be repaired and have mold remediation to rent it out, but the neighborhood has gone down in quality over the years and we are hesitant to have responsibility over upkeep of the home.

Or you can hire an engineer and have them write letters explaining quality of work, materials used etc to verify that the work was done correctly. 

Their lack of procedure and other processes should have little or no bearing on your landlording, and usually it only takes a bit of explanation to help a quality tenant understand that.