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→ Automated property management software could streamline it.Over the next few months, Michael slowly started letting go.

Historically used online software without much issue.Now that I'm looking at the settlement statements from 2004 and looking at a sizeable depreciation recapture hit, I came across a number of questions / issues:1) I believe in 2010 I incorrectly set my basis (I did not include the parking space and upgrades to the units - granite, flooring, etc.).

Do you not realize that If one software worked, do you think any other software would still be in business?!

If you’ve got property and aren’t well-versed in an accounting software I’d recommend starting with a good accountant and quickly adding a good bookkeeper.

Are you finding motivated sellers via the typical route of using the prominant software platforms like propwire and propstream?

There comes a point where having a real estate-savvy tax preparer outweighs your time learning a new software. 

Tracking can be done in property management software, a spreadsheet, or even a piece of paper and a pencil, as long as you can account for who's money is in the account.

As I understand it, many brokers provide this software to their sales agents as well.

You have to complete Schedule E if you have rentals.You should check if the turbo tax premier version allows the filing of Schedule E.With that said, using a software like Turbo Tax will assume you to understand what is deductible.If you work with a tax professional, you are more likely to have an accurate return.