Im just used to the area, however I was heavily considering Virginia because of how cheap it was to live on the coastline  (comparative to MA) I could buy significantly more there, however I would have to start over with looking for a new job and all that headache over again. 

So for these, you just need to work out how much less than ARV you care to go.But if you're talking commercial (5+ units), then yes, rent is very important in helping determine value, because their market value is heavily influenced by the market cap rate there!

While you certainly can try the MLS for this area, as I'm sure you've already found, this area is pretty heavily-followed and you'll have to be quite tenacious/persistent if you go w/ that strategy.

These are people marketing themselves heavily, working full time (and then some) to pick up new business.

Yes, I will have to rely heavily on the property manager.

We are heavily invested in B/C-class here, and doing really well...we find great properties very inexpensively here on "the streetz." 

There are jobs, infrastructure, great location, many jobs for young professionals, of course HOA dues weigh heavily on the return on rental incomes plus other expenses that occur but otherwise, is downtown a good investment considering “location, location, location”?

For example, I generally don't care about anything but actual cash flow, so the other numbers like ROI and IRR don't weigh very heavily on my decisions. 

I suppose a good example would be -- if you were to buy a property whose interior was straight out of the 70's (heavily outdated but in mint condition), what would you be updating/putting money into before putting it on the rental market?

I hope you're heavily armed for the trip!