The marina at Praia do Vittoria in 2008 had plenty of room for the JAC as well as other boats, unlike Horta. I don't think you would be in the way at Praia at all. Most skippers were meeting at 'Tropical Point' Restaurant of an evening for a drink around sundown if you would like to join us. I don't know if it will occur this time but there were a few events staged by the local council for us, such as a bus tour of their half of the island and a drinks session - you may be able to tag along on those, if they are so generous again.
Anne Hammick's 'Atlantic Islands' is generally thought to be the best book on the Azores. Anne describes herself as a Jester Groupy and in 2008 was asking all the Jesters for input should we note any changes. So it must be good.
Passage plans rarely survive the first gale.