Is this a factor driving up prices? 

Factor that event into you math and see if you still like the deal or what it would take.I have spent the last 20 years working for a global manufacturer and I am not too worried about off shore manufacturing - if he has not been wiped out in the last ten years (incl 2008-2012), he's probably going to be fine.

How many current mortgages is not the important factor... it's their combined balance.In most cases you'd be paying off both the first and second (and any other liens) at settlement and the seller would walk with the difference... in this case roughly $20k.

Personally, I don't think schools are that big of a factor for rentals in most areas unless you only want to invest in A class neighborhoods.

Obviously like you stated, taxes and VA limits will be different for different states and countieswithin those states so looking at what you can afford to live within your means in case of vacancies is a big factor. 

I have had a plan set in my head for a few years now that my first big purchase would ideally be a multi unit where I can live in one unit and rent out the others.

As of now, I put 20% of my paycheck into a Roth account where my employer matches 5%.I have had a plan for a long time that my first big purchase would be a multi unit house or a duplex, ideally a 2-3 unit building where I could live in one, and rent out the other.

Does anyone have a Triad commercial broker recommendation, ideally looking for multifamily exp.

Factor in a bump for FHA and a bump for Multi, should be 5.1-5.25% at best.Have you shopped around to regular residential mortgage brokers as well as your local bank?

Take note that the building is ideal for a daycare center, as there is a large, fenced-in yard with a playground and the building has a number of classrooms as well as a side room for an office.