As much as I hate the smell of cigarettes, I dont think there’s any way to prevent tenants from smoking. 

They think that asset protection planning is immoral because it prevents a creditor from collecting on a judgment entered by a court. 

@Ned Carey How exactly can we do an addendum correctly and what to avoid/prevent that makes it incorrect?

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.