As always, consult a lawyer.

The existing triplex is detached and built along the outer edge of the property line -- probably long before the current zoning rules went into effect.

Talk to your tax person / lawyer for the best guidance on if you should move it into an llc or not. 

Apps such as AirDNA, Your Porter, Google Suite, Zapier, when utilized together can effectively handle the 75% leaving you to simply take up 25%. 

With the state of the insurance market in FL, combining these 2 locations onto a single policy will have little to no effect on the premium. 

One tenant is a landlord himself and the other is a lawyer and they both seemed to think the lease was OK :) The tenants like to pay 3 or more months at a time. 

If you plan to hire a rental broker have you consider how the debt service coverage ratio might be effected by paying a one month broker fee

I would love some tips on how to book keep effectively when you aren't big enough to hire a book keeper but want to keep your finances straight for the accountant come tax time.  

I know this doesn't help you, but this is one of the worst side effect of letting late-payers stretch out the late-paying.You could try a frank conversation about how things need to change, how you need that rent on time.

There has to be a world where there are more options out there for the consumer/buyer to choose the level of service they want (full service, limited service, and self-service) and effectively get back part of the buyer agent commissions as a form of a refund -- or just have more leverage in the transaction because they aren't represented.Thoughts?