I have a close friend who constantly drives up to the white mountains so can definitely understand the draw.

While this may be risky in other ways, you'd be able to continue to grow your portfolio without taking as much equity from your income producing properties and possibly sustain your continued cash flow with them. 

The majority of homes in Cape Coral sustained some type of damage.  3 months after the hurricane, there were still blue tarps everywhere, debris at curbsides, fences and boat docks down, etc. 

These are top drive-to destinations for much of the Southeast, so short-term rentals here can generate solid cash flow, especially during peak seasons.The area is also seeing steady growth, with more infrastructure and amenities being added to support visitors and new residents.

She can set up payments to be paid on the 1st of the month and no one is driving 24/7. 

The main factor is will rents cover the debt liability and can you sustain 3-4 months of no income to cover the debt? 

They go into the sad state of the economy and particularly real estate valuations (properties depreciate, not appreciate like we're used to) which is what drives a lot of Japanese investors to the states.

And then the last hurdle is that driving miles between your home and your rental properties by default is considered to be like your "commute" to work, and your commute doesn't count as business miles. 

We help run the numbers, set up showings and video record them, and load up everything in a Google Drive folder.

I'm betting he'd drive to that area.