SAFD:
we usually plan our trips about a year in advance. We jumped into a more concentrated effort to earn rewards points through various Chase cards over the past 2 years (and had fully funded a cruise for our whole family including airfare and overnight lodging with them before COVID restrictions stretch out enough that we cancelled) and will continue to work on those. DH is an electrician and it’s easy for us to meet the signup bonus spending requirements when he is wiring a new house or 2.
For the past trip we points them to pay for:
-our hotel in Detroit the night before our flights
-airfare roundtrip
-our rental car
which “only” left our dvc rental, food, tickets, and souvenirs. We could also use the points to pay off our credit card bill, and the other cards’ earning is a lot quicker than on a Disney 1% rewards card (though I’m considering a Disney card just for the 20% discount perk.)
our grocery store runs a special a few times a year where you can earn a $5 “reward” for every $50 in gift cards. Which we stack that deal with whichever card has a 5x point earning for grocery stores at the time. And that way we earn more points and use the rewards to help pay for current groceries. It’s a win-win. And I can spread it out over a few different major holidays, so I’m not buying $2-3k in gift cards at once.
When DH gets paid for a large job we have a trip jar he will put a few hundred dollars in. When he does a scrap-wire recycle trip he will cash that check and put that in the jar. I tend to squirrel away cash when I get it (returns, birthday, selling baby stuff on FB, winning my fantasy football league

) to fund the smaller up-front stuff like registrations.