While I don't believe tech will be the end to residential realtors, I do think that whatever you do, it would be wise to adopt and learn new relevant RE technologies along the way to stay ahead of the game. 

They'll probably stay a few years or longer,probably won't trash the house when they leave, maybe you hire a prop manager and outside of an emergency you don't do that much.

VA loan is awesome however I personally feel as though home prices and rentals are ridiculous and unless you're throwing down a decent downpayment or staying here long term, it's not worth it.

Any thoughts or rule of thumb when upgrading your primary and still stay on investment goals?

When you do stay in house for few hours to make sure no leaks. 

I dont have an issue moving into the KCMO market and I think I would prefer to stay out of south JOCO unless I find an unbelievable deal.I have a few questions;1. 

Rents went down in 2017 and pretty much stayed flat.

You found one that will, and maybe those fees help them "stay in the green" on their balance sheets for those loan sizes. 

Get ready for a fun and fulfilling journey - the obstacle is the way, stay with it!

As long as you stay within the guardrails of this general strategy and consult proper legal and professional advice along the way you will be fine--Again with my post, and I may get flak for saying this, but a lot of people are actually hurting you more than helping by saying that you need to have everything figured out before you get started.