Make sure to do your due diligence when selecting a property management company to hire.

Lenders desperately need/want business especially in this interest rate environment (right now, the main source of mortgage loan business in Florida is rehab financing as a result of the hurricane damages) and one way the big players differentiate themselves is by streamlining the process.

This could be just specific to the real estate industry, but in both recruiting and cybersecurity consultants (hackers for hire), the ones that start their own business/consultancy, are the ones who after spending 2 years (usually exactly 2 years which is when recruiters will message them), the high performer will either 1.

I'd say start the process of securing your HELOC if you havn't done so and spend time analyzing deals and determining what type of investor you are looking to be. 

I don't know if I can sell my wife on moving into a fixer up but I assume the idea there is to repeat the process with the new house.

What's a friendly foreclosure process?

But consulting with the town would be good to try to understand what they're permitting process is like.

Everyone in real estate will be incentivized to upcharge your friend along the process hurting profitiability. 

Depending on the volume you would be submitting, find a company that does not have high monthly minimums and can walk you through the process if this is your first time using.

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.