The Charlottesville Area Masters of Real Ale meets on the second Tuesday of every month at Timberwood Grill (in Forest Lakes near the airport) at 6:30. I attended this past week and joined officially. 30+ folks in attendance and I found them to be a friendly group.
And in regards you other question, I thought I'd start with a Red Ale. I'll likely stick with the boxed kits for the first few batches before switching to partial or full grain.