Being prepared for these hurdles can make all the difference in achieving long-term success.

Unlike refinancing, which involves taking out a new loan, recasting keeps your existing loan terms—including your interest rate and loan duration—intact.

Owner-occupied commercial properties generally get better interest rates and terms when compared to pure investment properties. 

Must have tools: you need some type of evaluation metric and/or tool that you are comfortable with and are willing to walk about from a deal if it doesn't meet your requirements.also, a deal is a term for a transaction, not to be confused with a "good deal".

Quote from @John Brown: Quote from @Katie Miller: Are you saying you would long-term rent it from your friend and then run it as a short-term rental? 

In terms of finding a property that "works," I think you are absolutely right, there are probably better markets with more reliable cash flow.

If he has a $5MM loan in place, what was that used for / is it coming due/ was it short term/ etc.?

If your rental rate is below the market anyway, a Tenant might consider this to be win as they would get the lower rate in the beginning and just rise to the level they were looking at everywhere else.Step clauses can be written right into the lease, or created by using 3 month lease terms with an auto-renewal at the step up rental rate price. 

The term "reasonable" is going to be redefined.

I have found there to be a real shortage of long-term rentals in Ludlow and the surrounding area.