I feel I must correct myself I'm originally from Upper Marlboro, MD but I currently reside in surry va.

That is including my own personal residence.  

However, I live in California which is notoriously aggressive on this point (making any LLC owned by a California resident pay at an $800 LLC tax for "doing business in California" just by merit of living here), so my viewpoint may be skewed by that experience.

I currently live in Germany working under a 3 yr contract but would like to get into my first deal.  With technology being so prevalent, is it impossible to find and close on a deal completely online while only using ...

It's already automated for you.Yeah I put STR insurance on my condo and primary residence by calling my insurance company and asking if they were familiar with short term rental set ups.

In between that time, we also brought a 2 family home in Brooklyn, NY as our primary resident.

So this means we have no mortgage on our primary residence.

Yesterday I had a rather confrontational professor at the preapproval stage ask me to "match" 3.625% on a 30YF no points 90% LTV no PMI jumbo primary residence because someone at a 1-800 number from a website quoted him that...

I am looking for a home loan for a primary residence, but needing it to be a portfolio loan due to having rentals and self employment income. 

Which is why I'm here.My best guess is that, worst case scenario, a new A/C or heat pump would cost about $4k (I had one installed in my own residence last year).