I always tell clients it costs me zero $$ to send an offer and worst case they decline.

Where I see mistakes made in the note space are:1. companies turn into marketing and education - they lose focus on underwriting and managing their business.2.

Their pursuit of cash flow normally leads them to the worst of the worst neighborhoods where the spreadsheets never capture the accurate operating expenses and no consideration for neighborhood fundamentals is part of their analysis.

From the sounds of it, I won't be making that mistake.  

Then, run a rental stress test on the new STR assuming a worst-case scenario—like converting it to a long-term rental with a 30% cut in future rents.

It would be a huge mistake to help your friend get into this rental. 

The worst lenders I have dealt with are the ones with underwriters in one time zone and origination department in another, branch manager in another that don’t communicate well with each other and end up over-promising while not being able to deliver.

@Kim LeduffIn our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.The City of Detroit has 183 Neighborhoods we’ve analyzed.

You may end up needing to go through the whole foreclosure process which can take a lot of time and cost a lot of money, and you may end up getting the property back in much worse condition than when you sold it, potentially with a squatter in it and months of lost rent, and in a worst case scenario you will be in a much worse position than if you had just sold it outright.