@Matthew BruzekWhat state is this in, there are also departing home programs which are bridge loans that will work with you and be short term financing to buy a home while you sell your other

Control of property, with only ___ down, and payments monthly of ___, for __ term.

Its a short term pain that ends with a long (not even to long) term profit from my experience. 

It's important to carefully consider your options and what will best help you achieve your long-term goals.

Unless you plan to room rent long-term, you should make sure your room leases expire at the same time. 

My biggest REI shortcoming is that I am not an expert on construction, carpentry etc and I know I have been taken advantage of a few times in terms of inflated repair costs.My biggest lesson from this is to collect 2-3 quotes for large jobs before awarding the project to any contractor.

Cash flow, long-term appreciation?

The property currently consists or 3 furnished short-term rental units.

When you underwrite a STR also underwrite it for long term rental as well.

I understand if funds are not available it is easy get blinded by what saves the most, but if multiple people are telling you that it is a bad idea mostly likely is because they have learned that most of the times or never, saving in the short-term doesn't payoff.