However, I believe FHA with low down has to be owner occupied, so that might prevent you from getting another deal that isn't house hacking.

I've also set up a partnership to do some fix-n-flip projects, but again, finding a good deal has prevented moving forward.

Insurance of the two rental properties you'd plan on buying- Utilities and holding costs of the properties if not rented (like around here landlords have to pay water and trash and we have to keep heat and stuff on in winter to prevent pipes freezing and we have to keep AC on to prevent floors warping and such during summer)Those would equal the amount you need to be able to afford.

Imagine stacking new tenant protections to prevent removal on top of the Chicago RLTO.

Before you move, I would cut back any encroaching trees, repair any masonry or concrete, and do any preventive maintenance on the septic or sewer system. 

I am trying to do an ounce of prevention for the pound of cure.

Usually a mortgage company once notified will step in and pay the taxes to prevent their interest in the property being lost, but not always.

I’m running a pretty busy rental but it seems like there is always something wrong (broken drawer, sprinkler head, clogged drain etc just to name a few).

Safety - Learn about Crime Prevention Through Environmental Design (CPTED) and employ the concepts at your property.

What would you do to try to ensure that the PM company is more pro-active in preventing damage to that extent in the future.