One of my rental properties suffered water damage and I'm wondering if I should file an insurance claim or just eat it...?

TLDR: If we stop using it as an apartment (not planned) or if it suffers more than 50% of it's value in damages (fire or other act of god), then it would no longer be grandfathered in and must convert to SFH.

I need to put down some plants and 8" down I hit a cement wall, may be an old septic tank. 

Blocked condensate pan, dirty air filters, clogged pump, low freon, unit dying, vents not properly installed, air conditioning unit too small for square footage/airspace, exhaust blocked by plant material or stuff stored, animal inside the unit?

As a result, it suffers from some of the same issues the Midwest does as a whole, and for the past few decades has not seen the same kind of growth as other parts of the country i.e west coast and sunbelt.

So after I replaced all the sewer lines under the basement floor to the property line I had one installed $500, (had to get a permit & use a lic. plumber).Then when the city was replacing sewer lines in the street several of our neighbors homes suffered basement flooding with backed-up sewerage.

@Michael Plante thanks!

We would like to "plant a flag" in the U.S.

So basically you want to make your neighbor suffer so you're not suffering alone?

I won't use the names of the people I've interacted with as I believe this is more of a reflection on how Chase home lending conducts business than each individual person.tldr; Use Chase home lending for a mortgage on an investment property if you want to suffer and risk losing your deal.I got a pre-approval from Better.com.