Basically the outskirts of main cities.

You're right, I should have said once a year or more....because one of the main benefits of the inspection is to have a professional on-the-record.

The main thing I check to see is if the record of the estate shows that it has real estate.

From what I got from the info I was getting regarding land co tracts , the main benefit is if you are offering terms to the buyer.

I should also mention that my main goal right now is cash flow rather than appreciation, because while I love my job, it doesn't pay me the income Id like.

I built an ADU where the front house was technically a Triplex and back house was an ADU but the ADU couldn't be more than X% of the total area of the main house. 

In others experience is this return worth the risk given Multi-family environment ie supply, interest rates, project specific risks, illiquidity risk, and more specifically the Preferred Equity subordinated tranche risk (this sounds like just a Mezzanine loan without recourse).

My hesitation stems from the fact that I am unable to wrap my head around how this will affect the overall STR supply in vacation markets.

Your returns in investing ultimately come from exchanging terminally abundant goods (fiat dollars, debt/future fiat dollars) for terminally scarce goods (high quality, supply constrained real estate).Selling to go into cash isn’t of interest unless I have a short term need for that cash or am funding another purchase.

The main items that need to be specifically outlined are your expected time on market for the property and the minimum amount that you're willing to accept for rent.