Detroit would be a solid option if you're strategy involves a little more risk for potentially higher cash flow. 

Our current tech stack is a mix of Buildium (very clunky), Breezeway (great, but limited without a PMS), Xero and Google Suite tools with lots of spreadsheets involved.

There are a few options(1)You can get connected with the larger wholesaler firms in the area (2) go through PCPAO site and skiptrace the buyers of similar properties as yours, (3) hunt down the agents involved in the sale of properties similar to yours or go to local REI meetings and pitch it to the investors there. 

And this does not even involve business or real estate!

Quote from @Scott Mac: Every investment anyone makes involves risk.

Are there going to be banks involved, creative seller financing or all cash? 

Continually communicate clearly with all parties involved to make sure that expectations are as close to realistic timelines as possible.

I'm involved in too many things, but that's what happens when you have a family and kids to support.

However I am struggling to understand and evaluate the risks involved with cash out refinancing 2-5 years down the line.

Find an older one who'd rather sit back and get the interest than the higher return higher involvement of another flip.