I can't answer all your questions but let me comment on availability. In Aulani's short history, June has seen unusually heavy demand. Its the start of the American summer vacation period, so there are more families traveling to Hawaii. Perhaps more importantly, most of June has been in a cheaper season than July and August; thus, many members try to save points by booking dates in June rather than in July or August. In 2016, the seasonal disparity between June and the rest of the summer will become even more pronounced. Aulani's
point chart underwent a reallocation in 2016 and July and much of August are now part of the more expensive Premier Season. An Ocean View two-bedroom that costs 483 points a week from May 6 through June 26 jumps to 588 points beginning June 27. See this
DVCNews article for more info about Aulani's 2016 point reallocation. This change might put even more demand on the villas in early and mid June.
If you are flexible with your dates, I think you'll still have a good chance of getting an Ocean View two-bedroom in June 2016. But I would make sure to book as soon as your 7-month window opens.
If you are going to San Francisco and are a fan of Disney, consider adding a visit to the Walt Disney Family Museum. We visited WDFM in October 2013 and thought it was well worth the visit.