After all my careful plans, the airline canceled my flight! I ended up having to stay the night in Miami anyway, and get a rapid Covid test at the airport. And then got taken out back to a Covid quarantiner at the St Kitts airport, to prove that I was safe, because my paperwork hadn't caught up with my file. (The revised approval came in at 5pm, an hour and a half after I landed.) If it wasn't current, they were putting me into a van and whisking me away to quarantine. So that was... interesting. If I wasn't so tired from the travel, I might've been concerned.
The good news is, if you're traveling through major airports, they have the rapid testing centers to help in case of flight delays. So you should be safe on that count. Other hoops, all I can do is sympathize. Our original trip was delayed by over a month because we couldn't get the paperwork approved to bring our cats with us!