I'm thinking of just letting the HVAC go until both the heat pump and air handler (circa 1983) need to be replaced and renting the unit as-is.

In claims the squeaky wheel gets the grease......you can squeak for yourself don't hire a PA.

My plucked out of the air guess is a trust might add $1,000 to the cost of a deal. 

Reason being is you are unfamiliar with the other market & you'll need to hire other people to do all the work for you. 

Will you manage All or hire a property manger?

I've debated just focusing on one or two areas of work like flooring and painting, and demo perhaps and then hiring out the rest of the work.

If you are going to hire someone, that number needs to go up a lot. $50 for repairs on a home built in 1964 seems way too low for me. 

Hired the wrong contractor to rehab, big mistake!

Try also, Patriot Title or Momentum Title.Keep in mind that if you ask the title company to hire the attorney to draft docs, that attorney does not represent you because you are not the client. 

I plan on hiring someone to look at properties for me, $50-$70 to walk through the property, takes videos and pictures for me.