to answer some of the FAQs:
This was a trip by
"Keren Tosfes Yom Tov". This is an organization that promotes not talking in shul during davening. In preparation of the yahrzeit of the Tosfes Yom Tov they ran a major drive for people to undertake a קבלה not to talk in shul (even just for a day) and you entered into a raffle to go on this trip. Every shul had a gabbai (who got a ticket for his work) and based on the amount of people in every shul that signed, there were a few winners per shul.
Our company PIR handled the entire 'trip' part, flights, airports, food, hotels, buses, events etc, but I personally was only involved in the charter/airport arrangements
Why SWF? many reason, but not limited to being busy summer season, last min arrangements, would have been a challenge to get a slot & terminal space at JFK/EWR.
SWF gave me a lot of new and complex challenges, but given the nature of the airport, they were excited for this and willing to do stuff that would have been unheard by JFK/EWR, such as the preflight simcha
Why Eastern? we needed high Y config aircrafts, and a scheduled airline during peak summer season (with meltdowns every other day) is very difficult.
This also gave me many new challenges, some underforseen till it was too late and messed up, many things like this caused a major delay to depart, but BH after that everything went smoothly
Hope to be able to share a TR next week iy"h