I have narrowed down five different US cities where I would like to begin my investing journey and plan on picking one in the near future. 

A good investor agent using a good team, will tell you off the top of their head in 3 seconds every neighborhood by class, risk profile, and be able to evaluate asset condition as well.Your job is to pick a strategy...

-Any other behavior you can pick up on to indicate interestThen they put in the offer:-Are they the best PRICE or the best DEAL?

And eventually, they also fail financially, because over time capex exceeds cash flow.So I am very much in favor of @Tim Ryan 's idea: pick a market and grow roots.

I work with a local GC that picks up projects (fully or just specific tasks).

Green is good yellow needs to be looked at and Red is there is something wrong.. you simply walk in and pick up a copy of it on the counter..

When you choice who is going to service your loan what are you looking for? What is the most important to you?  (Thanks in advance)

I went through applications for about a week and I'm glad I did rather than picking the best from the first 2 days listed.

Also picked up co-hosting units.

If I HAD to pick one of your 3 options, I'd probably go with option 3 because it's likely the one that you can achieve the quickest... especially if you aren't concerned with cash flow.