if Yom Tov ends at 8pm and they are 1/2 an hr away at best must be at gate by 9;15pm , so even if you daven in the room and do Havdullah back in NY. Getting all the bags into the car or cab (if theres a rental car to be returned Forget about it!) checking out. Id still say it will be a very hairy experience
It leaves no room for anything that might pop up, hway construction, car accident, forget a bag at the Hotel or something very important, flat tire etc etc
It might workout but No Way would I ever if I have a choice put myself least my whole family into such a Lousy situation. Id rather loose my deposit and spend more $$ and stay at another program.
As for bags being dropped its an issue that depends on each Carrier and each Airport. Ive dropped of my bags for an Intl flight on CO with 25 mins till departure time, and had AA deny me checkin since it was 2 mins passed their 40 min time limit, DL as well. CO has denied me when I was 3 mins passed their cut-off at PHL
if a person must be on a flight no ifs ands or buts then I wouldnt play it so close, in my opinon its asking for trouble although its very possible none will surface after all is said and done.
Co has a 30 min before shut off time except for 6 or 7 airports where its 40 mins SAN isnt 1 of those, again its doable if everything is done to the min w/o any problems but wont be w/o worry and hassles
