The benefits that come with them can be attractive for sure.

Thanks.It’s definitely worth a conversation with your neighbor, but as others have pointed out, they might see it as you benefiting more than them.

Furthermore, whole note investments benefit from an additional 0.5% annualized yield and are entitled to a share of any extension fees charged to the borrower."  

Having time to do the work was the biggest benefit.

Their success speaks volumes however, its a bit much for me to stomach for a potential benefit. 

Longer Tenure in HomesData from the National Association of Realtors (NAR) shows people are staying in their homes for a decade (see graph below):This increased tenure means homeowners benefit even more from home values growing over time.

The investors that I work with find this benefit one of the most important. 

There are plenty of STR-savvy CPAs who can help you navigate the rules, maximize tax benefits, and make sure everything is done right.

How much weight do you give to the cash flow benefit of cheap debt when the property is priced above market?

While short-term rentals in areas like Kissimmee, Florida, can pay for themselves and offer lifestyle benefits, the ROI typically doesn’t match what I see from my traditional portfolio of long-term rentals in North Texas.That said, short-term rentals can still be a great choice, especially if you're drawn to the area and the opportunity to combine personal use with investment income.