I highlighted what I think is the most important statement of your post. If that's what you want, MD may not be what you're looking for, and I'd look into points further south.
I'll try to answer your questions with my own opinions:
1. It's easier, for now - I'm sure the powers that be are looking for ways to subvert the current "shall issue" status.
2. Yes.
3. The climate is the same with the exception of the state now being effectively "shall issue" for CC permits, but ultimately this is still not a gun-friendly state.
4. I don't like the state's firearms laws, and my goal is to leave the state, if not the region - southern PA or just over the line into WVa is the current goal.
Ultimately, I'd like to move to a state where they aren't trying to regulate everything, and I'd like to move to a state where it's a little easier to shoot without worrying about the mass of population. Another goal would be to go somewhere I can set up my own personal range on my property and not be bothered when I use it. A couple of months ago I was back home in Nebraska with a friend where we were shooting at a guy's personal range at his house. That was a good time - just the two of us, doing what we wanted, when we wanted and how we wanted.
Regarding the weather, we get about the same weather as you - again, I'd consider points further south unless you're trying to stay somewhat close to NJ.
