In your opinion, is doing the work I mention above a capital improvement or an expense?

Do you have specific cash flow goals?

In my experience these are the levels of how financial fraud is doneLevel 1 - The “sponsor” is a fraudster from the beginning and the entire investment is a designed fraud designed to steal the investor's money Level 2 - The sponsor initially intends to operate legally and honestly but the temptation of easy access to money, usually fueled by addictions to drugs, sex, partying, etc. leads to the bad decision to line the sponsors own pocketsLevel 3 - The sponsor intends to operate legally but a crisis in their life resulting in a need for money leads the sponsor to “borrow” from investor’s funds with the full intention of paying it back ( which they are unable to do).Level 4 - The sponsor intends to operate legally but the assets under their management incur substantial loses; the sponsor attempts to cover up these loses by “temporarily” borrowing from one investor to pay another or submitting false results.

Whether it is litigation or surveillance I would do whatever it takes to protect yourself and your investment 

The only thing we probably didn't do was tear out walls.

You could do #1 since we have done that with self-managed properties.

I have played with AirDNA and heard of Pricelabs, but how accurate are these sites with their estimates?

@Eric S. new britain. that is your answer. i invest there. i spent my whole life in CT besides the last few years. i know the area well. i own a few multi-family properties there currently. i went CCSU in new britain and lived in the town for 10 years. its an incredible source of cash flow and, in my opinion, the current mayor is doing all the right things. i actually see growth happening in that town, compared to the rest of CT that is struggling. happy to help in any way i can. just let me know!

Where do I look from here?

So, if things do go sideways, it's much harder to negotiate your way through.And, provided your loan is structured properly and closed with a competent title agent, I see no greater risk working with a private lender than with a traditional one.