Virginia isn't that hilly, it's just hilly compared to FLA.... I think the cassette you'd feel the best with is an 11-32 or if you have a long cage RD that can run one, an 11-34.... or just buy a new long cage RD that can handle the bigger cassettes..The new shimano 105 5800 can, I know that... and have your wrench put it on and lengthen your chain a link or two and get it running super smooth...

but it's kind of hard to make reco's w/o knowing your level of fitness in terms of climbing... If you really haven't climbed anything in a good while, I'd say being over geared is better than being under geared... meaning, better to have those extra gears and not need em' than vice versa....

I'd also run a compact 50-34 crank if you have one...