Thanks for all the great input. We've always used Cape Air in the past but the cost this time would be about $2100 for the 3 of us. $1100 over IC. Never had an issue with Cape Air and I've brought my same 24lb laptop bag, 2 large suitcases between my wife and I and even 2 dive gear bags as well. One time I even brought my drone which has its own case. I'd love to bring my drone this trip too, just not sure we'll be able to manage, although it may actually meet the size and weight requirements so we'll see. I'm going to see if I can pair down for this trip, maybe I'll bring an older Microsoft surface. I need to bring something though since if we were to test positive for our return and had to stay I'll need to get some work done.

One the plus side at least we are on the first flight of the day so worst case if something goes wrong maybe we'll have more options.