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

Yes you can get in without "military" involvement. 

If an early buyout opportunity arises, I’m happy to secure a solid return for all involved.

I have very rarely sold a property over the last 35 years and the income properties I hold now cash flow very well with not to much effort involved.

The title attorney involved had open communication with all parties on this and an addendum was added to the contract stating this.   

She didn’t even have to get involved with tenant issues, which is a win in my book.But here’s the flip side:Not all property managers are created equal.

You must know something about it already, since you got involved in it. 

While the traditional approach involves buying a multi family property, living in one unit and renting out the other - with rising prices and interest rates; others have considered renting out bedrooms as unit spaces. 

Offer to intern, find a way to get involved.3rd - If you find a deal, you can then find financing! 

For your first question, writing a scope of work (SOW) involves detailing all the tasks and materials needed for your project.