Is it okay to plant now?
Budget your purchases to include irrigation. I used to live in Norfolk. Nothing sucked worse than when 100 degree temps hit for the week while I was on vacation = dead garden. With some dedicated irrigation and a timer, I'd plant just about anything.
I loved McDonald nursery on Independence (I think there's one in Chesapeake, too. Plants are on the pricy side, but they have a excellent selection and knowledgeable staff.
- check your soil: is it sandy? you might have to add compost.
- check your drainage rate: dig a small hole, dump some water in it, watch and wait. If it drains quickly, pick plants that like good drainage.
- spend a day noting what the sun does in your yard. What areas are sunny, what are sun/shade, what are shade. Pick plants accordingly.
- think about how you want the yard to look in 1 year and in 5 years. Note the mature size of the plants you like and plant them accordingly (you don't want to move a large shrub or tree because you planted it too close to your foundation/garage/driveway).
For VA Beach I would do some research on Xeriscaping. I'm sure your local extension office has a pamphlet or info on this.
If I could only remember to THINK about what I was doing before I did it.