I've seen a people make this work successfully in Tulsa, you'd just need to be sure your goals align and the contract is set up correctly.Out of curiosity, what interested you in rent-to-own? 

This cpa/real estate podcast has quite a bit of info on all the STR tax components https://podcasts.apple.com/us/podcast/tax-smart-real-estate-...

I hear of all these great profits that are being made investing in real estate that has a major “business” component, like small assisted living properties; rooming houses; sober living arrangements, etc.  

We in our lease addendum have language that the property is X years old and may require components to be replaced which is not uncommon and no rent reduction or hotel will be provided.

A well-defined mission aligns everyone’s efforts toward a common objective.

A house hack is a solid way to get started as long as it aligns with your long term goals.I agree with @Samuel Diouf and @Jackson Ebersole's comments.You'll want to consider the competitiveness on Long Island.

In Mass, that means that all components are double-wall, non-corrosive (fiberglass). 

I am of the "never Communist" camp so there ya go, that's my alignment. 

Private money lenders are a key component in the fix-and-flip market, facilitating a dynamic and fast-moving segment of real estate investing.

If it was my deal, and I found out about something, whether legal or not, I would think that my investors have a right to know, and it would be my duty.I can see your values did not align with this individual and good on you for breaking apart.Gino