We're after a multi-family unit to purchase so we can rent the other apartments.By day, I'm an AI researcher but looking to build some additional cash flow through rentals.

Any additional suggestions, advice, guidance or even cautionary tales would be greatly appreciated.

You mentioned some small rooms, this often happens when a large addition is attached to an older smaller house. 

Using the rental property calculator, Cash on Cash ROI is -7% for the first year, and doesn't become positive till year 11, after we've had to invest an additional 46.2k to balance each month.

In addition, if there is an emergency, (I defer to fire, flood, and blood as my definition of emergency) you do not need to provide notice.

Seems like your experience as a title agent will be a huge benefit as you continue on this journey - and you'll be a great addition to the forums with that expertise!

While there may be ways to reduce your tax liability after the end of the year(IRA Contribution) most of the tax reduction is done throughout the year.

I realize I can just wait it out and cashflow nicely, but I'd like to get the ball rolling on additional properties here at the beginning (happy to hear arguments for/against that too, btw).The solution I was thinking of was to do some sort of intermediate loan with private money until the 6 month period is over and then go with traditional lending at that time. 

In addition, I see two thing looking at your analysis. 

In addition, short sales are "as is" so an inspection is for my purpose and my lendor only.