For your first deal, it might be beneficial to try doing some of the simple work yourself so you know what goes into it.

Of the many strategies I've looked into, House-hacking and short-term rentals piqued my interests. 

In terms of the areas, you will be best served driving it.

@Michael Carbonare The rent to own strategy has been good to our business model as a long term buy and hold investors. 

Shorter term deals though, they will hold 2 to 3 years, sometimes less.

Long term, your property is going to up in value; likely way up.

A lot of rehab lenders will account previous reno expereince when it comes to terms.

Property taxes will likely be reassessed based on the transfer value, so confirm local rules to anticipate potential increases.If you hold the property for at least one year, you can use the equity as collateral for a construction loan, aligning with your long-term financing plans.

The income amounts look to be long-term rental (which they are and came in 30% lower than what the STR average did) and 2. why did the appraiser look at homes 20 miles away to compare to when there are PLENTY of rentals in town...

They will get the highest price and the best terms for their property by marketing it professionally and exposing it to the maximum number of retail buyers, which means putting it on the MLS with an agent.