Craig,
Your project is by far the most interesting I've seen all week. I started reading your description thinking "Wow, Logistics & Freight, Boring!", it didn't take long to see that you're really passionate about this project and the company you're building. It's been quite a while since I got to work closely with someone with that kind of passion.
Very Up-Front you should know that I have lots of Backend Development, Analytics, Systems Administration, and a breadth of Web Technologies experience and knowledge that I'm constantly working to improve. I also have some Copywriting & Editing experience. I do not, however, have a much design experience or talent. I've spent the past few months on a personal development hiatus trying hard to change that. I'm definitely not a cheap template factory, I'm at a point now where I can comfortably turn someone else's idea for a design into a reality, and where my abilities fall short I am close enough with people whom I fully trust subcontracting to or even providing a direct referral for if you prefer.
Your minimum viable product of "payment, download and upload, and quick quote", is very doable within a two-week timeframe, and I can start adding the other features in your preferred order of importance afterward. I also don't think it would be much trouble to do the sites separate or joined, it's really your preference.
I look forward to hearing from and seeing this project through with you!
Cheers,
Jay