If you haven't done so already, I'd have your team start working on initial numbers for your refi.

The rates seem fair, the initial process was somewhat smooth, but as time goes by things are dragging out and the communication is getting worse. 

I agree with @Abel Curiel on house flipping.You may want to consider a less sexy but long term viable option.. buy and holds with some initial value add potential, wait 2 years for further appreciation and rents to grow (given market uptrend continues at mild rates), then refi into another deal.

Can I still take a delayed financing loan out while still retaining a certain amount of equity in the home if my appraisal after repairs is higher than the my initial investment in the property.

Given the massive military presence there, I would recommend making your initial focus on renting to other military if the BAH numbers work out for what you need.

The hardest part for me initially was remembering to update it.

I have a team of Architects, Builders, Lawyers, etc. already set up and doing initial planning but the amount of capital and experience is something that i'm just not privy to yet.

Never say never while congress is in session. 

Are there any suggestions you guys have to get us over that initial "hill" and start this journey confidently?

If you had little to no debt (DTI: 5%-10%), currently renting, your initial REI goal was to fast track your way to be able to quit your 9-5 job with replacing it with positive cash flow, main goal was to acquire as many doors as you could, had 100k to start, and still had cash for reserves…Would you continue renting and or seek out a primary residence where you could house hack (keeping your DTI low, so that your able to still acquire rentals) or would you first acquire income producing rental properties and then use that income to eventually help you qualify for a primary residence?