skip lagged is an interesting app to help look and find open 1 way tickets that can be combined into a return package. I've used it a few times to get some good deals. However, when flying with family the cost is the cost, sometimes the benefit of saving a little money is offset / negated by the convenience and sanity of your family during travel! lol... We love Alaska and always fly, however, we just couldn't get the flights we wanted at the right price so we shopped around and just managed to stumble on a release day at United and so booked it for less than half of what Alaska wanted. Granted its not direct and we run the risk of being dragged out by our hair kicking and screaming, but its going to be a fun and interesting social experiment! haha....
It would be great to book as far in advance, but there are issues with having to come up with the money that far in advance which can often be problematic. I also think that there is an element of flexibility with dates at hotels due to the fluctuating deals and discounts. Saving $500 on your overall flight costs can easily be wiped out by the difference in discount at 2 nights of a hotel. So the problem we have is more based around the hotel costs as they will be the ones that make or break the budget. We then work hard to get the flights we want at the price we can afford. It's kind of putting the horse before the cart but financially it works for us.