Quit that and go work for someone who is in the industry, even if you work for free.  

Well, here is some out of the box thinking from someone not involved in commercial real estate nor the hospitality industry, but very involved as a patron of restaurants...First question... is your location good for restaurant traffic and does it have adequate parking?

Should this be a red flag about me entering this industry?

In the event that a lender seems to be un-informed or incorrect as related to VA lending guidelines, one might be able to reference said handbook or maybe even email a copy/link straight to the loan officer to clarify… since they are more familiar with the specifics of the lending industry verbiage.b.

Not really difficult you can either cash out some funds depending on where your current loan balance is if you wanted to retain your current home and buy the multi or you can sell your home potentially tax free to purchase the multi (section 121 - principal residence exclusion).

Makes me believe that is either not an institutional loan or the property is risky like land or industrial.  

I also went to school for my real estate license but that was only so that I could learn even more about the industry and gain connections...

I work in the healthcare industry as well!

And send them a mail piece telling them you noticed they purchased the property at Acme lane and if you can add them to your exclusive cash buyers list.

I plan on attending my first REIA meeting on the 17th of this month and really look forward to meeting people who are in the industry and making some new friends, at the meeting and on the forums.