Figure out which damage is normal wear and tear; ignore it.

If the tenant caused damage or liability 3 times for different things, that should not necessarily affect your insurance premiums. 

If the house is dirty in which it attracts pest, they your tenant is responsible for pest control and damages as I'm sure when the house was leased it was "pest free" If they flip the bill for it, which you have every right to expect if it's clear their mess is the problem, then that might give them incentive to clean up.

Yes, the $5,000 worth of work is a guesstimate, assuming I'm only doing touch up on flooring, water damages (maybe), etc.

I need to add that this tenant is great as well, usually quiet and hasn’t ever been late paying rent.The condo has a full bathroom that  doesn’t have any windows, thus no real way to air it out.A while ago, the tenant noted that mold was starting to show in the ceiling and for me to take care of it. 

Currently; we have 3 properties (One house hack, one long term rental, and one Air BnB) The house hack is breaking even, the long term rental cash flows about 700 per month, and the Airbnb makes about 10k per year. 

You will almost always win.After Hurricane Ike, I had $100,000 damage to my beach house.

Think of it this way: the liability policy is in place to protect you from your tenants (ie. slips trips falls, dog bite, etc); the umbrella policy will most likely be used to protect your properties from you (ie. you are at fault in a car wreck, damages in an unrelated business, etc).  

The Deal1 4 bedrooms 1 full bath (Upstairs)1 1 Bedroom, (In the basement)Current asking price $179,9004 Bedroom rent: $1,2301 Bedroom Rent: $540 ( Ideally Luanne and I would take the 1 bed after we are married)Newer windows, siding, furnace and central air. 4BR unit is super spacious with laundry on the main level and new carpet in bedrooms.

They're practical, cost-effective and can either be discarded or repaired depending on the damage without much effort or expense.Having a uniform appearance is nice particularly if you're handy and/or self managing as you don't have to keep extra materials around for each property but rather a small inventory of items that can address a repair in any unit (i.e. an extra plank, a can of paint, a knob or handle, etc).I say find a hardware store you like best, sign up for whatever incentives they offer and build your list out from there.