Weak- Cashflow is most important factor, everything else followsStrong- Potential appreciation is most important factor, everything else follows. 

All of those are more important than finding the "best" market in the US.The Midwest gets a lot of attention lately, but that is not without challenges.

Its not as important that you use the exact right words or even ask the right questions necessarily.

If neighborhood class is important and you are planning on investing any significant amount of money, then its worth having boots on the ground to see, smell, and feel the area.

Valuation for Property Management 3X to 5X Seller Discretionary Earnings or 1X to 1.5X Annual Revenue, depending on how well established the brand and reputation is in the market, market share, number of units, scalability, etc...Transaction Structure, never buy a Property Management business for cash,  you must include an earn-out structure or provision to protect the purchase against clients/property owners leaving post-transaction.  

Do I have the gist or am I missing something important? 

Having a good mentor to help you navigate will influence the level of difficulty and how you maneuver so I think it’s highly important.

Infact, I would have to show tax returns on LLC for two years before I can include it in pre-approval. 

What should I do in these towns to understand the market but more importantly the city to see if I would want to live there after I graduate college?

It's important to be aware of the risks involved, including unfamiliarity with the market and potential travel costs.