As someone working with my father's home improvement business for the past 11 years, I have worked on multiple flips deals, just not on the investing side.

So if I was in your shoes, I would put a little work into the curb appeal to improve that first look. 

Tell him your concerns, see where the breakdown in communication is, and figure out how to improve it going forward.

Anyway, the HOA is saying that not only do I need the typical exterior paint color approval and any sort of window shutter approval, etc, but there are HOA "fees" associated with improving one's property.

I enjoyed reading the details of your business plan and enthused to improve my own and add more detail.

I'm currently Active Duty Air Force and will be getting out this December.  

Lenders also don't like to see these liens so even if the buyer wants it their lender may not.Maybe when you sell the house you can pay it off, with or without prepayment penalties, but if this is the case do the math to make sure this improvement is worth it on your fix and flip project, it may not pencil out, it normally doesn't.

Not easy and would love to hear your story as this progresses and see what areas you did well and where you could improve.  

I'll be posting some questions on here soon about how to improve my real estate game.

I expect that values and rents in those areas are going to improve fairly well over the next few years because of that.If you are planning to live in this property, you really need to decide 2 things:1) Do I want to live there?