A tool I have communicated to the cleaners I ultimately did not hire was to ask them if they would be interested in working on an "emergency" basis just in case my new hires are not reliable... they like this opportunity and will likely make it a point to deliver as a chance to win business.

Tell them as much specific stuff you are looking for and get to connect with that agent one on one so you both have clear communication of the goal in mind.

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.

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. 

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.

Their website, communication, and online portals are usually garbage, and when I have 40 documents to submit each closing, it drives me up a wall to send 100 emails back and forth.

Costs and quality of communication are difficult.