Glen, I'm not aware of a way to automatically categorize items.

I have assumed their leases and added an addendum that includes a few items (no auto renewal, new payment address, etc… ) which I am planning on asking them to sign.I sent non-renewal letters about a week after closing (early April), which gives them way beyond the 30 days' notice.

One important item to note: if you receive passive losses from bonus depreciation and do not have a use (or only a partial use) for those passive losses in that calendar year, they can be used in subsequent years to offset gains as well.

I send my Tenant an itemized list of charges as required by law.

Being a builder, my first thought goes to the construction type items: Tile or wood floors, vinyl shower kits, high quality wall paint like Behr Marquis, solid wood furniture, good appliances not cheap rental ones, easy to maintain yard outside like DG, artificial turf and gravel. 

Prosper's explanation was that many providers deny claims for the particular items/incidents they call out.

It goes over specifically what LTR insurance policies don't cover, but a couple of the items would carry over to STR as well.

If any items were damaged as a result of this leak, I would 100% tell the tenants to reach out to their renters insurance, assuming they have it.

So you had lots of vacancies in the weekdays and then people having parties on the weekends.Lots of locals smoking weed on the front porch / blasting music on front porch, plus worse, that I wasn’t fully privvy too.Airbnb is making it harder and harder to screen Airbnb tenants (a quick Google / FB stalk is impossible without last names / photos being shown).A party starting to kick up at 2 am that you’re watching from your outdoor cams hundreds of miles away and your 450k home on the line is a terrible feeling.Anyone who’s been doing Airbnb long enough has horror stories, big items stolen, thousands of dollars of damage, or worse.

Start working through the items one at a time and you will see it is not really that hard or impossible.