@Chris K.One method is reviewing appraisal data for the local county office to determine allocations between land and house.

Ensuring that I'm making the most of BP is high in my priority list.

The way I've narrowed it down is by:Gathering data from all 50 states (population growth, median income, crime, price-to-rent, etc.)Filter out states that have rent lawsFilter out blue states (not because of political beliefs but from my understanding they have less rules and regulation and I believe that in the current climate we're in with COVID and all people are going to flock to areas that don't have as much regulation)Highlight states that people retire in more than othersBecause of short-term rental becoming a trending way to invest, filter out states that impose regulation/rules against short-term rentals using platforms like Air BNB, etc.Also, using ZILLOW, I type in my parameters (homes under $125,000, sqft.

There are other data sources predicting the exact opposite. 

Before you throw $500 at the idea make sure you have the data. 

Permitting will be huge in ensuring you are compliant with all building code requirements, especially if you ever plan to resell.

We would like to interview a couple companies to ensure that our interest are aligned on how the property will be managed.

Many accredited investors want to see your failures more than one super successful deal in order to see how you bounced back and what you have learned, as this ensures some more security for their capital investment.

There is a ton of data on here covering nearly everything. ;)

Since you are owner occupying the property, the loan underwriter is likely going to want to see the leases to ensure you can occupy.