One thing to watch out for is the financing aspect of it - could be a hurdle getting a loan if the transaction is "non-arms length" - i.e. between "Friends" - might be worth looking at seller financing too

I would suggest finding a lender that treats your transaction with the same care and attention with which they would treat their own.

I'm part way through Craig Curelop's book, and starting to see what the market is like.It seems like a lot of the properties will have negative cash flow even after the first year when we move out.

@Randy AchiTo start flipping houses, learn fundamentals through books, podcasts, and online courses, build a network, start small, and practice repairs.

My thought is is use the Rent Ready feature of reporting his payment history to the credit bureau so it can work in his favor as a trade line, but I'm wondering if this is an unnecessary added step since he can already pull transactions on his bank side. 

It’s been booked ever since.

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.

Though fee schedules vary by company, generally speaking, you'll pay more up front for checkbook control and less over time, since the full custodial companies will have transaction fees not to mention the red tape of going through the custodian for all transactions. 

We have an STR in Swannanoa that wasn't damaged and have had several week+ long bookings since the storm (including Army Corps of Engineers, etc). 

Thanks Canopy Title is great with assignments and wholesale transactions!