If they do not pay, you go to the district office for that jurisdiction (most of our rentals were in Rochester/New Brighton/Monaca) and fill out a form, pay a fee, and wait.

What's the annual tax funding from property taxes for the district?

It's a diverse area with everything from run-down areas, to blue collar neighborhoods, to gentrifying neighborhoods on the upswing, to upscale historic districts.

Ideally, I will keep investing in both small and large multi-family but I want to be efficient with my personal housing costs by rehab/renting (developing a portfolio of cash flowing SFH's or small multi-families) or house-hacking if I could find 3/2 quads/townhomes in decent school districts. 

This area is generally categorized by School District.

I have been scrolling through listings on Zillow and redfin to keep my eye on the market and to get a good feel as to what prices to expect and my current plan is to but a house that needs updated and to live in my first house to a year while making the updates to try and maximize the sweat equity.My spouse wants me to stay in the current school district which kind of makes things a little harder because its more of a rural area and there is another school close by.

For instance, I just looked at Orlando FL and if I'm reading it right, it appears that they don't allow STR on residential (R) zoned districts.

Public policy in many areas considers residential uses within industrial districts may increase hazards to the residents' health and create significant fire and safety burdens on the safety forces. 

I have property in Tucson (SE side, nice area, Vail school district) and in the SE Valley (of Phoenix). 

I still see alot of potential, caprock district is my favorite place so far.