Carpeperdiem, as RatmansWife mentions, Silver printed our boarding passes for our SJU-MCO flight when we checked in at EIS. That's always been our experience. To me, the two time critical issues are:

1) Does Silver leave on time from EIS (since COVID, we are 0 for 4)
2) How busy is the security line at SJU (earlier this summer it was ugly......even mid-week)

Good luck to you, and have a great trip!