Move on.If they say, "maybe" or have lots of questions about the details, then move forward and pursue.#3  TRUST.   

I live in Florida and willing to move to whatever city I can implement BRRRR estrategy, here in Miami doesn't seem possible.

Is it worth moving forward? 

Our current plan is to purchase our first home and live in it for 2-4 years before moving to a new home and using this first property as a rental, so my fiance and I are currently in the market for a home that we could use as our residence during the offseason and then use as a short term rental or something like that while we are away for 6-7 months.

if you want to move to a LCOL market and house hack there, that's great. 

I'm a Navy public affairs officer, so I move every couple years, but I'm currently in Germantown, TN (near Memphis), and I've been interested in RE my entire life.

Selling and move on.  

Quote from @Christi Wolverton: First time in 3 years of mid-term renting that I had a credit card denied two months after client moved in.  

Looking to find duplex or something along those lines to reside in and then eventually move upward.

Lenders will want a letter from your employer that states you are allowed to work remote from where you currently live and that this move will not affect your income.