Have a vacation planned for six nights to celebrate my 20 year anniversary which occurred 3 years ago but due to covid the trip kept getting canceled. It is six nights divided into two places, a short stint at each. just found out my daughter needs surgery it is scheduled for the day after we get back. My daughter has a congenital condition which requires surgery almost annually, don’t ask, I’ll save that for another post. with all of the flights being canceled I am nervous about going. Should I cancel the trip, cut a day off? Hope for the best? maybe we are not meant to go?

I would cancel and plan an even bigger one for your 25th anniversary, which is only 2 years away at this point and which you can schedule for next year. If your dd has surgery annually, try to schedule it at a different time of year, or at least build in a few weeks buffer before/after. But the risk of traveling, getting covid, flight canceled, etc., would not be worth it to me. Plus, being married is all about riding out these ups and downs together. Doing the right thing for your family and not just for yourself is one of the reasons you've made it this long. Happy anniversary (:
Can you take a trip closer to home (within driving distance) instead and postpone this one (yet again)? If you absolutely need to be home for the surgery, I would not take a chance on flights. Or, as you mentioned, you could add a buffer day, but then I’d cut out one of the two places, so that you don’t waste a day traveling between them and get to chill at just one place.