For me, I plan on spending around $1,000 per ticket - and likely driving ~5hrs to Newark for direct flights and saving a lot on those. The problem I have is I can either be flexible with timeshares or flexible with airfare. Usually the hotel vs timeshare difference when getting 2 rooms overwhelms a couple hundred in flight costs, but certainly not always.
Interestingly enough, I don't think airfare is curtailing trips any more now than going back to at least 2007 (kind of when I started paying attention to / paying for my own trips that included flying really). Flights always were "a lot", and still are "a lot". That said, I think in reality they've come down in price because throughout all the inflation, the priced dollar amount has stayed around the same, with the main difference being losing one carry on bag (I think when I was pretty young all the airfare included 2 checked bags, I now pay extra for one and the pricing seems similar).
And I think that's why the flights are full - real purchasing costs for flights are still near the bottom in history, especially compared to the "golden era of flying" when only "rich" people could afford it.
The thing about flights is I still haven't really found that I'd "lock in" to even United from Newark to make the mileage cards worth it. The deal alert stuff sounds more promising, but I'm still not really comfortable with booking a timeshare and then hoping I find a special flight deal in time. For hotels sure - I can always book a Hilton somewhere, but again, that adds a lot of hassle and cost and loss of a kitchen etc...
Now opinion aside - I think it may just be me not really thinking / trying it - but say I'm planning on flying from Newark to IDK, San Diego (for MarBrisa) next March. What should I set up to look for a deal? If I don't find one, do I just buy the tickets "normally" at ~2 months out like I usually have done? I feel like those "cheap flights" sites never seemed that worth it, but I see people using skyscanner here and I've also seen momondo - do I just set up an ongoing search there?