Those deals give me hay fever, mostly from people who don't want me involved. 

Do you recommend we use accounting software? 

Hoping to make connections with folks who are investing full time, keep each other accountable, partner on deals potentially  but most of all MOTIVATED

Never twice.I recommend you start a relationship with an accountant, since your understanding of taxes is shaky.

You want an accountant that can help you strategize and who is responsive when you want to know the tax consequences of the decisions you are making throughout the year.Good luck in your search.

I feel like there's some pretty cheap properties out there, and with financing involved I can get in the game for pretty minimal cash-out of pocket.

Our long-term plan involves eventually vacating our current residence to rent out both units.

And when you account for appreciation that doesn't appear to be changing in the next few years, you could lose more by waiting a year for the "best deal" instead of paying $10-$20k more right now and starting to save from your house-hacking venture. 

Account Closed the first thing you need to do is is find the source of the 1566 sqft.

Run the numbers and you may be better off keeping your money in a deposit account that earns 5% (or look for something even higher) than buying a rental.