I've never even itemized.

Your tenant leaves after a year, you get in there and find dirty floors and carpet, have to touch up or new paint, various broken/damaged items. leaks under sinks ruining cabinets, etc...

And just for clarification, I see our follow-up system as entailing two different items.

While we have tried to make a point to update as they items break (upgraded bathroom when tub broke not just replace).

I bet their were no regular inspections and not real option consideration or earnest money to be lost if not purchased, like 3 - 5% of FMV.A Security deposit on a nice home does not cover many damage items of being in excess of "normal wear and tear."

We need to do a few more things on the outside (gutters/ fascia), but the big ticket items are done.

I also have  accounts At the end of the year my CPA does all the tax items and tells me how much I owe.

Not demanding the item be repaired right away.

I think the main things are to find good (good= check references for other out of state investors, ask about items you're concerned about being taken advantage of) "boots on the ground" support i.e. property management, RE agents and possible contractors to do more major work. 

I'm in our procurement department, so I spend all day working with our suppliers of both goods and services, helping folks at our resort properties sort through issues, finding strange/large/expensive/hard-to-find items, and bidding out items that we need for various projects to generate savings for the company.