I found all sorts of things to reference for an eviction including excessive damage to the property, signs of an animal, lack of yard maintenance, oil spill on driveway, smoke detectors removed, the unit smelled of smoke, appliances that came with the unit moved off site ect... 

It’s obviously leaning heavily and one already fell and damaged property.

The only thing that comes to mind may be insurance-related, so I'd recommend speaking to your insurance broker to see if the cost may be different due to fire damage could damage more units at a time.

Even if you have enough for a down payment and closing costs, there is always a chance the furnace or AC goes out the first time you try to turn it on (typically this would be caught by an inspector), or some major damage happens that insurance doesn't cover.  

He has to prove damages and you haven't stated anything a judge would award damages over.Putting in insulation is a good investment for you long term. 

Quote from @Kathleen Park: I recommend you educate yourself on "ordinary wear-and-tear" vs damages, depreciation, and your state laws.Do yourself a favor: buy "Every Landlord's Legal Guide" by NOLO.

On new builds the maintenance is lower but there could still be damage.

You probably recoup the 5k in ARV, but Old North Milwaukee is an economically challenge neighborhood, so manage your expectations.Avoiding frequent turnover, tenants who don't pay, damage property or cause other issues is the name of the game to achive long term profitability.

Hello BP community,I'm a landlord in California, and I'm dealing with a situation where my tenant is refusing to pay rent for the time during which mold repairs were being done due to water damage from a neighboring unit.

Treble damages are available under the statute if its proven to be a pattern or practice.