If rent is $1500/unit and his portion of PITI is $1k ($2.5k PITI -$1.5k rent of other unit) that still leaves maintenance/cap ex (~$500, two units at $250), vacancy (~$150), pm (even if self managing include the cost because it is work - ~$150), misc (book keeping, office expense, asset protection (umbrella or LLC), etc - ~$100).Sum total is negative ~$400/month compared to renting. 

Not really surprised since every accountant sets up their books slightly differently...and then there are the owners who don’t do good bookkeeping and I wouldn’t expect any software in the world to eat their financial “reports”.How much did they say it costs for RedIQ?

By the time I reached 150, I had my wife helping about ten hours a week with bookkeeping and I had a full-time office assistant.

There was one time that my bookkeeper did forget to make the payments for a couple months. 

To try and help your accounting, I do bookkeeping on the side and I have found Wave to be a decent free software. you can link your accounts to it and "teach" it to code for you so maybe it would help you to take less time to do your accounting and have it formatted right away for you.

Its all a matter of bookkeeping...I would also look around the board.. its posted more than once a day.. 

OR better yet, have enough inventory that it justifies and supports a full time staff(handyman, office/leasing, bookkeeping/collection), so that you are mostly supervising. 

As I am entering the transaction in my bookkeeping software I can't figure out how to categorize the cash deposited back into my checking account, it sure doesn't seem like income to me...  

As its been discussed nearly daily on bp, the "right" legal structure to invest in residential housing could be anywhere from sole proprietorship to a really fancy, i.e. expensive, LLC and trust structure that many lawyers will happily charge to setup for you (and some CPA will love to charge you to do all the tax filings and maybe even your accounting/bookkeeping). 

Maybe it is bookkeeping or running errands.I agree with John, be skeptical.