I haven't been there in a while but Virginia Beach area had a really good scene when I've visited and of course there's the beach aspect too. Winters are worse, but... give and take.
Having grown up there, VB sucks. Very few skate spots for a city its size (probably due to the flatness of the area). The spots that do exist are really spread out. It's not unusual to drive 20 mins to a spot, skate it for five minutes before getting kicked out, and then get back in the car to do it all over again.
The city skateparks are fun enough, but get super crowded due to there being a low number of them compared to the amount of people who skate. Helmets are required (park nannies get paid to sit at the park and enforce the rule) and as of recently you have to pay for a park pass. I just drive to Norfolk, a neighboring city 20-30 minutes away from me, and skate the park there since it's helmet-free and you don't have to pay to skate.
Cops are pretty zealous about skating; I think because of the low crime rate they don't have too much to do.
Traffic in the Hampton Roads area in general blows, especially in the summer.
Speaking of summer, it gets really hot and humid. I remember one time I was skating a spot at night last summer around July and it was 95 degrees. At 10:00 PM. Fuck that.
Not much of a club guy, but the night life is pretty shitty from what I hear. There are some cool bars though.
Everybody and their brother skates, surfs, both, or adopts the look. As a result the skate scene can be really clique-y. Shit's like high school sometimes, it's embarrassing.
All that being said, it's not all bad. There are definitely some cool people who skate in VB, living close to a nice beach is rad, and the winters are VERY mild compared to the rest of Virginia. DC, Richmond, and parts of NC are all within a few hours driving distance, providing a good amount of close options for filming trips.
I personally was not a fan growing up skating there.I guess there are some similarities to Cali though haha. Traffic, mild winters, and a dominant skate/surf culture.