I think tax benefits should be secondary to buying something that would work well as a STR.I would recommend you consult a tax professional to see what possible tax benefits you could receive from buying this STR.

@Shafi Noss Improving the land would be the simplest since there's already a driveway, electricity, and an old water well that needs to be jetted again.

One thing to think about is when doing heloc on primary if you want to refinance you need to get their signoff as well as your primary loan which could cause complications.  

Quote from @Dustin Wilkes: Well hello there everyone.  

All the water issues could have caused this as well.

The problem with Multi Family is that unless you or your partner have $10M or so of net worth and $1M in cash laying around as well as prior experience with commercial real estate, you can't get the loan. 

If you want to take pictures of some of the work you did, you could save that in a Google drive as well. 

We have investors and opportunities in both of these cities as well other some other similar markets not too far from there.

We want to get a few rentals up and running and then (if all works well) begin bringing other friends/investors in to invest with us.

Dear Fellow Investors,I hope this message finds you well.