We will then refinance our property and use our FHA loan again to repeat the process (while building our portfolio through other assets simultaneously).This investment was a huge learning experience.

Any advice on how I can make both of these deals work simultaneously? 

From tax perspective- Simultaneous 1031 exchange to avoid taxes. 

This can make it easy for tenants to apply at multiple places simultaneously, even if they are not fully interested. 

Insurance claims get complicated where there are simultaneous causes. 

I'm new to this journey and so excited, but simultaneously fighting to stay motivated. 

Here we will try to see what may happen in the future of housing prices by comparing the historical relationship between the case schiller housing index and personal annual income per capita (both on log 10 scale).In 1933 during the depth of the Great Depression, both incomes and the housing index saw a massive simultaneous drop.

My times of greatest stress, worst relationships, and worst times as a husband and father in general have been when I was trying to chase two opportunities simultaneously.  

Anyway, I think your best course of action is consulting both a CPA for the tax side and an attorney for the legal protection, preferably both of whom work in conjunction with each other and can advise you simultaneously.

This feels sufficient to me, as I'm also pretty handy and self-manage, and if a bunch of simultaneous repairs were needed, I would like dig in and try to do some of them myself.