For me, it has to be a data-driven decision: what is your current NOI, what would be if you replaced the boiler, how much will it cost, and how long will it take to get your money back...If the area and marketing don't warrant central air, I would NOT do conensors right away and just focus on the forced air.

This is not the cheap markets but the higher cost markets.This year I added a half bathroom out of existing space in a very expensive area. 

@Denver McClure Would be a good connection to make as he is in your area.

I live in the Washington DC area..the HOA/condo fees are pretty reasonable and the insurance doesn’t have the embedded risk as Florida (I don’t believe)

The property is in a solid area where Neighborhood Scout puts it at the highest rating for appreciation, predicting 40% appreciation over the next 3 years, and we'd look to refi or do a HELOC in 3-5 years to realize that gain, and I'd probably buy them out with my portion at that time.

I'm in Santa Barbara County which is impossible to make work so I'm forced out of the area.

So don't be confined to just areas/markets that you know people in!

You are going to want to find some good wholesalers in your area that can help you find distressed properties, or network/cold call some home/duplex owners in your area to see if you can find a discounted distressed properties, use the heloc to get hard money loan.  

Should I live in this house after and buy more property with the 100k or rent it out move and try to buy more property, the only problem is my area is so expensive a new mortgage would be more then what im paying now.

If not I would recommend looking up other AirBnB owners in the Covington area and simply asking them who they use.