I don’t like my tenants getting the idea that they will be charged anytime they report something wrong.That’s just my two cents without knowing the entire background on your relationship with the tenant.

@Tobi Isaacs this would be better answered by other investors in your market. 

As I approach my move out strategy where I will be converting my upper unit into a STR, I often think of guest interaction amongst the two units.

My wife (who's from CR) and I are early in the process. 

We’d like to work with a realtor who has experience finding properties like this who knows what to look for and can help us make a strategic purchase.

How well will it cashflow?

Quote from @Owen Wang: I am 17 years old and will graduate high school next year.

I'm actually hearing that it will be allowed for residential multi family as well, although haven't confirmed that.

Your VA loan will be crucial to your real estate investing growth, especially since it affords you the potential opportunity to own more than one property, depending on your overall allotment.For active military personnel, that conundrum of where to invest and where you will end up is always part of the issue that sometimes causes analysis paralysis so it's great you have one in VA Beach already.

I truly feel bad for people who have to work instead of investing in real estate, especially those with kids.