If you have a lot of family in OK, that can be a great place to start assessing since you have dedicated boots on the ground, as well as a reason to visit.Don't overthink the analyzing of markets when you are still figuring things out.

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

The only two ways to rectify this are (1) purchase the property far below market price or (2) significantly increase the property net income usually through some method of “repositioning”. 

Fairmont is a good little market!

There are a number of real estate Meet ups monthly in Calgary market advertised on Eventbrite.

What market are you referencing?

As for your ques if to wait, well, it depends on the market, in some parts of the country prices are still going up, slower, but still going up, other parts the prices are coming down, you know that area, what is happening there? 

I signed up for their investor profile because I am interested in the appreciation in the North Texas (or northern suburbs of DFW) market.

I know this is also a National issue, especially in land constricted markets.

For appreciating CA properties this could easily be a 7 digit step up in value but i would think in all CA markets would be significant.