Private Lending Attorney Here-First it depends if the person lending the money will be doing this on an ongoing basis - if so he may want to have a separate entity created for that business.As far as documenting the loan - I would recommend speaking with an attorney who regularly handles these transactions. 

I am in the lumber/millwork industry so have a good handle on that end of things.I saw in another post it is possible to invest in a duplex for $50K?

Given your circumstances, it sounds like a lot to handle all at once.

However I think I should have something in my rental agreement to handle this.

Challenges?

Challenges?

Being 1099 and not having guaranteed income is challenging as is, I'm essentially dipping deep into my safety net to fund this project but the last couple of years have been great and I'm eager to get started.

I would also look into how challenging certain city codes are with short term rentals, permitting, etc.

Challenges?

Challenges?