I want to know if the climate of the neighborhood is shifting for the good or bad. 3.

There is no climate control, security gate, etc, it is simply a self storage building. 

How do you address rehabbing and reselling properties during the winter months in the mid-west?...Any past experiences with being able/unable to move properties during the winter?

I tend not to do well with extreme climates...but I also am willing to make sacrifices to better the chances of success in my dream to have a successful real estate business, if all goes well, I can live anywhere right? 

One fantasy is to find an area in a warmer climate, preferably near surfing (for the husband!)

One thing Florida and Texas have in their favor is the boomers retirements and wanting to move to warmer climates and states with no income tax.

4) Will obtaining mortgages at similar rates (20% down, 4.65% APR in the current climate) be more of a challenge as our notional real estate portfolio climbs above $5,000,000?

In the current Colorado market climate (insanely hot) it will be totally ineffective because there is too much clutter and competition, and for open market properties with any potential at all there is fierce competition. 

They usually have foresters on staff that are very familiar with the local timber climate and would be a great resource as you identify possible deals.

I mean we hear about businesses leaving CA all the time for places like TX because of the harsh CA business climate.