She's either a liability because she's time consuming and requires me to spend more, or an asset because I know she'll be a good custodian of my property.3) I have another property that's in poor shape cosmetically.

With a consumer-buyer/tenant: JUST DON'T.  

All part of the larger legal framework to protect consumers from repairs by unlicensed contractors.

Flipping homes has a few down sides; first it's very time consuming, second it's risky, thrid it's taxed (usually) and fourth it's a job and not an investment.Have you thought about keeping the property and rent it out?

I rehabbing my first 4plex and it’s been the school of hard knocks....costly and very time consuming.

They said that  they “cannot legally” do this because of landlord-tenant laws and the liability of tenants complaining, then suing due to paying an unfair amount of utilities because another tenant over consumed.

This time consuming, and if the investor doesn't close, it's a total waste of time for the contractor.  

Unfortunately, there are newbies/ investors that are unscrupulous and have scammed consumers.

How it works out...Once all consumer debt is eliminated, and your net monthly cashflow from rentals is 2.5x your personal housing expense, you can continue buying/refinancing cashflow positive rental properties and DTI will work out to be in the Fannie Mae allowable range. 

.- Prepayment or early payoff penalties for consumers are a thing of the past for your vanilla conforming FNMA type loans.