The gas water heater is new (2013), and the electric panel is newer, though I don't know the age.   

Sure you can go hire your own employees, pay worker's comp,  pay payroll taxes, file your quarterly taxes, pay benefits, take the time to hire employee(s), train them to use your platform, and manage their time. 

In 2013 they added central AC, hardwired alarm/fire system, insulation, 22 new double paned windows, so it's been modernized somewhat. 

I've easily thrown ~$20K already, I've got a mortgage on the property, thankfully not causing to much strain on me, but regardless, i'm losing $ every month I'M Paying the mortgage and not a tenant.

It just makes both parties miserable and strains our professional relationship.A concern with MTM leases that some have is that tenants may leave in the middle of winter when it is hard to find a new tenant.  

Vinyl dual pane windows can be found anywhere/anysize for under 180 each.

Paper thin walls, single pane windows, which lead to hi electric bills especially in Florida, which tenants will complain about.  

and may put a strain on those relationships particularly if the homes never make it to contract. 

Adding loan expenses might strain the cash flow.

If it will strain you by purchasing a income house right now, I would hold off for a bit, continue to build your capital, and revisit your first deal in a year.