Would placing well in this jam help contribute to a higher likelihood chance of getting selected for pirate jam 2020? Or even better, would you consider letting a few finalists get guaranteed pirate jam admission (on their own dime) as an additional prize?
Pirate Jam 2020 is already completely full. The only remaining open spot in Pirate Jam is the Grand Prize spot being awarded via the Pre-Jam Skirmish.
This isn't an issue of payment - though being able to purchase a ticket does help (a little) in the general selection process. It's an issue of the number of boats we can fit into an anchorage safely (6~7). And how many guests can stay aboard those boats comfortably (3~5). And how many sponsors we get who pay for their own boats and/or teams. This year we have 3 sponsored boats out of 6 which doesn't leave a lot of space for those who would be willing to purchase tickets.
Ultimately it's just not a very big event - 20 guests and 10 crew aboard 6 boats. And that makes selection difficult... with there being more than a few people who've applied to join for several years who've yet to be selected.
A goal for the future is to have more than one Pirate Jam per sailing season. That would mean we could host ~40 guests per year and that would increase the likelihood of a place for those who've been trying to attend for several years.