I’m talking about getting thorough with expense estimates, factoring in property taxes, insurance, and a cushion for maintenance.

I can’t diagnose your issue from the pics (though it seems repointing needed) I can say that there are contractors in this area who will immediately jump to the $35k+ solutions when they see deferred maintenance on these types of foundations.

Differ the maintenance on the property to stop the cashflow bleed and hope for appreciation to save the day.

The plan is to put the rentals in SCH E of our joint return and file with TurboTax-We live in Florida-Leases under my wife's name, Airbnb app under my name, dedicated bank account for all rentals activity in the name of both-We have umbrella policy for liability protection for the rentals-We leverage some contractors (for example cleaning lady for the Airbnbs or lawn maintenance guy) that we pay >$600 for their services in a year and they are not our employees.

Beyond the Monthly Management, Placement & Maintenance fees, all other fees in our contract are IF EVENT -> THEN fees.

As you progress, maintaining a clear line of communication with your team, especially your property manager, will allow you to stay ahead of maintenance issues and tenant needs, keeping your operations smooth and your tenants happy.If you haven't done so already, consider outlining your goals and investment criteria with a property manager early on.

Marketing, screening, collecting rent, unpaid rent, maintenance, capex, insurance, lawn care, vacancies, turnover costs, inspections, and so much more. 

Or if you want something lower-maintenance, stocks or other passive investments could be a good option.What’s your next big financial goal now that the mortgage is off your plate?

We were able to buy low in a good neighborhood since the home was in need of some work, mainly needing cosmetic work and some deferred maintenance.

There are several things to fear money loss on a bad investment, government involvement in RE, bad tenants that cost time and money, hidden maintenance issues and/or land issues and the list can go on.Today, I don't fear money loss or tenants,  the big unknown is how much the government wants to get involved in either taxes or landlord/tenant issues.