No one else can answer what YOU should do only what they would do in your shoes and the answer is highly personal and depends on so many factors (experience, knowledge, risk tolerance, age, passive vs active, available opportunities, skill set, goals, etc.).

Any trade will give you a good understand of construction plus you can barter your skills with other trades.  

I've got a lot to learn (negotiating skills, estimating repair costs, how to assign a contract, etc.) but for now I'm just looking for feedback on my plan at the big picture level.  

My background is in staffing, so I have a lot of experience in sales but have never really envisioned myself being a realtor, and have really focused on learning and developing skills to be a RE Investor.

Similarly, ideally this produces outstanding cash flow that will improve your life.I think with your experience and your partner's experience, you have some good skills to help you succeed.  

Maybe you have more knowledge than you indicated, but what skills do you have that make you think you can flip a house right now? 

Here is an article that I wrote on ways to start with little to no money:https://www.biggerpockets.com/member-blogs/10145/70092-getting-started-with-apartments-with-no-skills-and-no-money

But really I'm here to sharpen my skills and learn from Investors.

Obviously to be purchasing deals of this size you’d have to know a little something, but let’s assume the buyer and I have an agreement that I find him properties @ an amazing discount because my negotiating skills are just that good (this is hypothetical).

Interview some managers, see what they do, and how they can help you, what their business plan is etc and hire on those skills versus fees.