If your firend wants to stay in the place AND has the funds/income to do so, they need to refinance in their name ASAP (as part of the process), not 5 yeas from now, not if they remarry, not 10years from now.   

Last but not least....A few members in replies have already mentioned why it makes sense to hold…….I very much appreciate ALL FEEDBACK, however I think it will be helpful to provide some added context as to why I am absolutely certain (and my CPA’s are convinced as well) on my decision to liquidate the entire portfolio and onceAs I educate clients on daily, income tax brackets as well as long term capital gain tax brackets in our country are more favorable right now than they've been at any point in the past 80 years.

@Gregory SchwartzThere's nothing passive about passive real estate income.

You can search this company on the web, but there is ZERO mention of his name in affiliation with the company. 

STR income: $170K/year with pool.

However, what if you prefer simplicity, limited risk, and are living off of the income? 

I do not have a traditional W2 job so I can't pursue the typical conventional loan or a FHA since I don't have income (hence the DSCR route).However, I've seen that most DSCR lenders do not lend if the loan amount is less than $100K.

Given your situation, a property closer to Nashville might be more advantageous for short-term rentals like Airbnb, as proximity to a popular city typically attracts more guests and higher rental income.

Sometimes, there is also a tenant already in place which means you can start generating rental income from day one.

. ==== Projected Income ====**Off Season**-$4,000/Month Rent Period: September - May (7 Months) Projected Income: $28,000**Summer 1**-$8,000/Week Rent Period: June (4 Weeks)Projected Income: $32,000**Summer 2**-$8,500/WeekRent Period: July-September (12 Weeks) Projected Income: $102,000**Optional** (Basement Apartment)-$2,000/Month -Rent Period: Year Round Projected Income: $24,000TOTAL PROJECTED INCOME: $186,000 ==== Operating Cost ====-Mortgage: $84,000 ($7,000/Month) -Utilities: $36,200Gas $6,000 ($500/Month) Electricity $6,000 ($500/Month) Internet $2,400 ($200/Month) Garbage $5,000 (Estimate) Pool $4,000 ($250/Week)Landscaping: $4,000 -Mowing: $2,400 ($150/Week)  -Clean Ups: $1,600 (Spring & Fall)-Weekly Turnovers: $8,800 ($550/Week)==== Legal Cost ====Summer Rental Fee: $20,100 (15% of $134K)Sandwich Rental Tax: $6,855 (15% of $45,700) NET PROFFIT: $38,845.00