Of course they will not but I wouldn't want to be looking over my shoulder my whole life waiting for boulder to run me over.

With Covid 19, lending in many cases is simply non-existent, in your scenario, you would shoulder this negative cash flow until that changes.

We’re all working professionals with a decent head on our shoulders, good work ethic, and limited RE investing experience.

Then you've got tenants that have a chip on their shoulder.

If they are uncomfortable paying $40 to get a living arrangement they will probably shrug their shoulders when it comes to other things around your property and will fail to keep good communication throughout their tenancy. 

I will say that the stress of having this off our shoulders and not have to hear him stressing out about it every single day is almost worth the $3k to me. 

Mine never have trouble paying the rent, as $550 is much easier for a person than if they're providing for a whole family and shouldering $1500 on their own.

Bear in mind the due diligence in finding a requirement like this wouldn't be shouldered by the bank/loan.

The ideas I've heard include attending an upcoming Note School for investors in Asheville, talking with hard money lenders to pick their brains, checking into tax lien/tax deed sales, and finding experienced partners that may be willing to let you "look over their shoulder" while they're going through a fix and flip, so you can learn, as a silent financial partner. 

For beach rentals run occupancy assuming 3 seasons high, low, shoulder seasons.