Answering the unanswered questions:
* Not all ryokan are family-run and there are a couple of monsters with several hundred rooms out there. Then again, it's debatable whether such a thing is a ryokan anymore, or just a hotel in disguise... not everything calling itself a ryokan is one.
* Having dinner and breakfast at the ryokan is a big part of the experience. At dinner, in particular, they pull out all the stops to serve incredible feasts. At most, but not all, ryokan you can opt out if you wish though.
* Bringing your own wine would be a little odd, as the food will obviously be Japanese and thus better suited to sake and beer.
* In a proper onsen ryokan there are no bathing times as such, the baths are open 24 hours or close to it. At a hot spring it's traditional to maximize your soaking and bathe no less than three times a day (once before dinner, once before you go to bed and once before breakfast), but this is up to you.
* Bathing facilities are segregated by sex, and yes, it would be somewhat rude to wear a bathing suit. Some higher-end ryokan can, however, arrange a private reserved bath for you and yours alone.