But both should only invest what they can afford to lose.  

We have done this for over a year now and this strategy has gone really well.We are very experienced in the STR space and understand that getting bookings is multi-faceted (ie. listing photos, reviews, amenities, PRICING, description, seasonality, etc).

Cash for keys is common, and frequently the part that keeps tenants from moving forward is not having an affordable place to go to.

Tulsa offers a fantastic combination of affordable housing, a growing job market, and a strong sense of community.

That way you are an alternative rental option for those that cannot afford a single family home.

@Julie J.My recommendation would be to wait until you can afford a home with traditional financing.

And unless you have very deep pockets, you can't afford to be that much off....So as has been said....hire a very experienced General Contractor and have them give you a budget number based on your SOW, (plus they will find other things that need to be done that you will not have seen).On your succeeding projects, you do a budget yourseld first, then hire the GC and compare numbers.Then, eventually you will be comfortable going all solo...but it takes time.

This ultimately why the $100k midwest single family homes are frequently discussed in these forums.....its what many are able to afford to buy.

Quote from @Alvin Sylvain: I don't know of any special protection afforded you by placing the property in an LLC.

Luckily this was a super cheap property so I could afford the additional down payment.