For men, the answer is simple: a tuxedo, literally with a black tie. If he doesn't own one, he should rent one, complete with a cummerbund and patent leather or other formal shoes. If the invitation says "black tie optional," he can wear a tux but can also opt for a dark suit with a dark tie instead.
For the Ladies. Women should wear a formal floor-length evening gown, no exceptions. Pair your dress with jewelry, heels and an elegant clutch.
Well, we need you partying all weekend (2-3 days) and there are lots of wonderful options. I'd check out AirBnB for the best options.
Yes, we will have valet available at Leoness Winery for you.
Coordinating a wedding with plated dinner can be fun and we wouldn't want someone forgotten. I would check your invite for number of guest and/or reach out to the wedding party for support.
4:30 PM PST gives you more then enough time to make it to your seat and get ready to party like it is 1999!