Capital improvements include expenses for improvement to the property, such as a new roof, new siding or major renovations.Capital improvements for residential property are deductible over a 27.5-year period; Ordinary repairs required to maintain the property in good condition, such as painting, fixing leaks and replacing broken windows, are deductible in the year they are paid. 

And then he had a chair broken, which was a $100 fix, and then he wanted to start charging everyone a $500 damage deposit. 

This will be broken down as $30k ($50k - 20k) taxed at depreciation recapture rate (25%) and $100k at long term capital gains tax rate (15% or 20%).This is my understanding but I’m not a cpa. 

The obvious was fixing things that were broken and bringing in Pest End to treat the property Lessons learned?

lots of broken picks in that space. 

Here a quick tip for when you are interviewing companies ask them this question "what are you steps to address a broken hot water tank"If they answer, send a plumber out and address the problem, you know they'll charge you an arm and legIf they say, they'll walk the tenant through trouble shooting steps like resetting the pilot light, you know they'll save you money 

I'll add that as I was reviewing properties I noticed some of the listings have property taxes and insurance broken out.

General condition issues like holes in the walls/issues with windows, broken flooring.

@Jessica Parker I have a cabin in Broken Bow, Oklahoma.

If there are pictures of it not being “broken” before move-on I’d get a handyman quote or have landlord do same to simply fix it.