If you are considering a CRM for a team, then you have to consider the ability to customize and generate management reports.

Many cities in the NW will require a permit to cut those down I know where I live you cannot cut a tree without a permit and you need to get an arborist to write a report that the tree is a danger. from what i see I dont  think the arborist would need to go on the other property to do a report but leaners can stay that way for years and years. 

I do not break them down into categories, however I explain what work was done in the memo line so if I want to know later I can print the report and add to an Excel spreadsheet.Attached are screenshots of a sold property.

This was not on the inspection report and did not present as an issue until I went through my first winter season.

Most all do a Cost Seg report as soon as they close.  

I'm working on launching a STR reporting product designed to make data analysis accessible for everyone, even if you're not a data geek!

I've done this, disputed with my bank and filing a police report.

The real question is whether or not they call it out in the report and send to the lender.

Planning performs a thorough review to make this determination including searching publicly and also checking to see if anything was reported to the SF Rent Board or a DBI complaint.

As far as the reporting goes, the rental income and losses will most likely be reported on your Schedule E - speak with a tax professional who has expertise in real estate.