I would invest into the furnishings and spending time marketing to try and get quality tenants in place.Let me know what you think of this strategy, anything and everything is welcome for advice or stories of your experiences in this arena. - JD 

Low priced houses, low quality tenants, low quality property managers, low quality contractors. 

Ensure high-quality linens, cozy blankets, and a well-stocked kitchen.

Mathew, From my perspective you need to talk with local real estate investors and a quality realtor to determine what is needed as well as paint choice options.

There's no guarantee a new HVAC will last but the one you have is quality and has lasted more than two decades.

Would the units be similar to your current property, or would it be lower quality?

I can find quality people to do what rehab needs to be done, but finding the right properties, keeping a stream of investment options coming, and negotiating the deals is harder to train in my opinion.

Quality are commanding high prices. 

At this point you just want quality conversations to happen, just like with direct mail, it's a follow-up game.I don't think your expectations are unrealistic when it comes to having your VA sound less robotic, they conversion numbers aren't that bad, they need feedback to get better and sounds like you're providing that.

Schools are one of the factors that drives quality and rise prices.