Emphasize how this arrangement could work to their benefit, offering steady income, avoiding a traditional sale process, and giving them the freedom to move forward with their plans such as buying that sailboat and sailing around the world.If they ultimately decide they’re not interested in selling, you’re still in a great position to continue your search and buy your own property in the near future.

Top searches at our beach place is pool, then pet-friendly, then water view, then water front.

@Ashley Kehr have you used the Search feature here on BP?

@Abel Curiel, When I first drove by this property in my initial search it caught my eye...out of the 100 or so properties i had on my initial list this is the only one that I had memorized the address of. 

If there is minor rehab (such as painting and cosmetic improvements) you can still close on a DSCR loan, however it may affect your appraised value, which could also affect your market rent if its a vacant property.

This would buy time to improve cash flow or explore better refinancing options.Ask Your Lender: Would they consider lowering the rate temporarily or extending the loan period while you stabilize cash flow?

As others have said, the best thing your son can do is run far from this deal, buckle down, save his pennies (he probably already is doing this), house-hack, and improve a property with sweat, hard work, developing a DIY skillset, and self-managing tenants. 

They may argue they couldn't pay you because they just made a $10,000 improvement to the house. 

There’s huge retal income potential if you nail that balance between improvements that wow tenants and improvements that merely look fancy but don’t justify higher rents.I’d also keep an eye on how your high end plan fits the local demand.

If the fence is shared and in bad shape, framing it as a mutual improvement could help.