Talk to your CPA and set aside any funds you may need for taxes.Given that you will have zero cash flow over the next 12 months, there is extra burden on you to ensure you are smart with the money and keep reserves in the event there is a problem (e.g.

Disclaimer: Im aware seller COULD drop asking price or that I COULD bring a ton of extra cash to the table.

But I'm only looking for extra $$$ coming in each month.  

I couldnt count "future income" so they think I was losing about $2000 monthly when in fact I would be making at least an extra $2500 with the new place.My buyers broker suggested a mortgagor that has many loan products including a 20% down nonconforming mortgage.

They know their capacity and are at it.You really have to be extra careful when considering people who recommend themselves. 

How do you make it work, with all the extra planning and expenses? 

Did you think about maybe doing the Air bnb option on your dream home to bring in extra cash a few times a month or more?

Pick up 2 extra jobs, move to a cheaper (or free) housing situation and live like a pauper (this is temporary sacrifice for Massive long term gains). 

All my extra cash goes into the company stocks and I don't save any substantial cash.I'm not really sure on how to calculate the ROI of this type of investing, but the re-invested dividends produce about $300 per month (currently) and the amount increases about $10 per month on average.

I tried to calculate what increase a garage was worth, an extra bedroom was worth, and a $/square footage rate.