The more pertinent question about #2 is why would anyone with a functional mind pay a $300 membership ($25 more than the season ticket itself) and do it months in advance for a "benefit" you can't use on the one night of the year you need it most. That is the one night of a season that you can't get anywhere near the concession stand (believe there is only one) unless you want to stand in a long line for a long time and miss a good chunk of a period.
Better idea is to just keep the $300 in your pocket and let them keep their finger food, snacks, popcorn and refreshments for that one night and the other 15 home dates too. For those other 15 dates you will do far better just spending the $300 you kept on a game by game basis at the one concession stand. You would have to average $20 of concessions for all 15 of the other games just to reach the $300 they want in advance for the membership. One member (or should I say likely former member) spending that much on concessions per game 15 times seems highly unlikely. In fact, I seriously doubt I ever reached that amount even once in the well over the half century I have been attending.
No, it is not overly difficult or time consuming to use the 3 or 4 line concession stand on anything even resembling a normal night. At least not after the two year fan ban. For the two seasons since, the average per game attendance (including Freakout) has been 2,225 and 2,251.
Conclusion: This one is right out of basic money management 101. The Pride membership has no financial tangible value of any kind. Keep your money!!!