Tom, I'd love to meet up when/if you're in the DC area. I would offer a place to crash, but honestly I'm not sure if we'll have a place of our own at that point! (we signed a contract to sell our house, settlement is Sept 28, and we may be staying with family after that)
If we have a place for you to crash, I'd love to have you stay with us. We can debate all these Apple issues in person

But seriously, Virginia is gorgeous in the fall. Autumn is easily my favorite season, probably because of how great it is here. My wife and I basically plan out a set of "falltivities," and announce them for any friends interested in attending. These things usually involve corn mazes, a haunted forest, apple picking, etc. Great stuff.
As for temperatures during that time, it's seriously anyone's guess. Our area is crazy with weather, and sometimes it's 80 in mid-October, but other times it's 40. Either way it's a great time of year, and I really hope you enjoy it here and everywhere else you go on your trip. Please let me know if I can help in any way.