I am a full time 911 Dispatcher and plan on building a portfolio alongside this.

Do you prefer a cash offer = less net, or financed offer = more net & possible hiccups along the way?

That way I could underwrite the deal alongside them to understand how the process worked and why they did what they did.

However my real concern is you mentioned that your bills depend on their ability to pay as well which implies that you don't have sufficient cash reserves to handle financial hiccups without putting yourself and your family in a financial tight spot. 

The only hiccup I have found from talking to other agents and investors is that as a full time firefighter, it may be difficult or improbable that I could be a successful agent being gone for 24 hours at a time.

With BAH the only hiccup I could see would be if there's a major difference in the allowance between your home of record zip and the mob zip.

My hesitancy is coming from the fact I will be managing the project remotely, and there is increased risk for hiccups along the way.

Helps to put it into perspective when projected alongside your potential returns. 

However one hiccup my insurance broker dropped on me is that he cannot find any insurance company to insure the detached unit as technically is an "other unit" like a shed or garage. 

After some google searching I'm having hiccups finding free "official/legal" leases for Colorado that I can alter and use for my tenants.