Purchase 2:  A 3 bedroom, 3 bath house a short walk to Poipu Beach. 

I'll get most all of my remodel money back out and be left with about 20% of my own money in the house - cash flow will be limited once rented.

A pretty spreadsheet doesn't matter because none of us know how accurate your numbers are, your level of experience, how many times you have seen it in person, and what other property anomalies exist.

I have a couple of 2/2 houses here in the area and I was contemplating making them mid term rentals for the traveling nurse/insurance company play, but I was wondering if anyone is in that space and if its doing well?

@Octavio Sanchezstart with a house hackgood luck

Could be that most landlords have a negative experience because the local housing authority is very anti-landlord. 

I'd also try calling the court house (or whoever issued the writ of possession) and ask them about options explaining that your calls to the marshall's office go no where.

Also, the ADU is 3 bed/2 bath and detached from the current house.

If the house value goes way up, the seller has taken a loss, as without the option, he could have sold for more.

Indianapolis hosts a lot of events so people travel into town for all sorts of conventions.MTR market is also strong as we have a lot of hospitals downtown as well as traveling professionals who need furnished housing.