DH travels frequently for work and has a Bonvoy credit card. He's using the free night award for the pre-flight stay. We are about an hour+ from the airport. It's an easy enough drive, but I have a 5am flight. In order to get there with a comfortable window for boarding, I'd have to get so little sleep that my first day at WDW would be difficult, especially as I'll be with a 4-year-old.
Our return flight is scheduled to get us in mid-afternoon, so assuming no major flight delays, I should be able to get home with low to moderate traffic.
Either way, I'll have time on both sides of my flight to deal with shuttle delays, should they occur.
Since we're in western CT, I usually fly out of NY, but the parking situation at LGA is completely ridiculous right now. Once I factored in parking, it was less expensive (and easier) to fly out of BDL, even with slightly higher airfare.