Not going to become "Joe Realtor" at a big brokerage, but the license will be quite valuable for our existing transactions and I think we will benefit from access to info on the MLS, etc. 

Hey @Tyler Hall, I think there is definitely some benefits to going to college just to get a basic level education but depending on where you end up going it could be tough to get a great return for your education.

That being said, @Jordan Moorhead, above, is a RE Agent who specializes in working with investors, he's set up MLS search for my criteria and has helped me gain knowledge while I'm currently out of state.

This person would make me money by gaining appointments because face to face interaction is where I excel.

My debate I am having with myself is should I consider managing my first property or two so I can gain the experience (Been there done that, got the t-shirt kind of deal) or should I put my faith into a management company from day one, freeing my time up for other opportunities?

Do you use the extra cashflow ($2000) to payback the principal balance, or to maximize the benefit of leverage you only pay back interest only for the first 10 years?

Ultimately for me buy and hold; he gains patina in the process and makes seed money for his next adventure.

In general, the larger the project, the more you'll realize the benefits of modular, especially with custom.

I know I'll have to pay capital gains regardless but wanted to see if there was something I'm missing here. 

I agree with all said above, but if it’s not the only way to gain access, use alternate means.