@Steven DiazFor anything construction related, I am not very knowledgeable, but there is a real estate group called The Mills Group in town that works a lot with investors and they themselves do a lot of flips so maybe they would be a good starting point.For STR I would do the two units separately.

Spend a lot of time there.

When looking for cash flowing markets.. a lot of investors, including myself, are looking in cities like Cleveland.

However their internal business systems leave a lot to be desired and have really messed us up. 

The ADU is a good idea for property maximization, but unless it has a separate driveway, it will push your rent in the main house down some because then you aren't renting a single-family house on a lot by itself.

In a perfect world that’s how I would start since it would be a lot easier than buying a home but I’m sure there’s some things I’m overseeing.

Wood ignites at 700F, fabric a lot sooner. 

Best case, you learn a lot, survive financially and trade up.

Theres a lot of content on here about house hacking.

The 2008 timeframe was different and in situations a lot harder than now, but this market will shape a lot of investors that found their new market, product to focus on, and/or to dive in deeper when times get tough.