According to my HVAC guy, it would've been next to impossible to get air to the 2nd floor without messing up the ceilings, not to mention the issue of getting cold air all the way up to the third floor.

There is some air sealing with the addition of loose fill insulation, yet this method will ensure an effective performance.2: The HVAC duct system & registers have to be air sealed.

It's great that you've dived in, and I applaud your thick skin in airing it all out here in the forum.

If so find out how much it would cost to convert.Also you do NOT want to be paying for your tenant's heat, they should be paying for their own and can keep it as cold or warm as they chose.Depending on price range of neighborhood I'd also consider central air, very reasonable to install at same time.Another alternative is to install a heat pump, cheaper to operate that elctric baseboard and has central air.

Same in the summer with 2 air conditioners on full blast even when no one is home they will still be running.

This weekend is a bit up in the air, but it's one of our options!

The property needs a bathroom, kitchen, air condition ducts (air conditioning does not flow throughout the entire house) and repair to ceiling in living room (rafters are exposed) I would have to spend some money if I just did a SWD and move renters in.

We also change air filters at this time as so few tenants will (even though we provide filters free of charge).The more often you can inspect, the better.

This December, I intend to get out of the active duty Air Force and joint either the traditional ANG or Air Force Reserves.I do not have the capital for any down-payment, so I'm thinking of joining a unit that is a few hours away, such as Charlotte, NC, and using the VA again to purchase a multi-unit with the intention of living in one unit once per month when I have to work.

He is with the Air Force currently stationed in Dayton OH and he does what you want to do.