1. Yes, anyone who shows 5 years Pro Experience will get their "sixth" season when the league rolls over. Additionally, anyone with 3 pro seasons will, next season, have 4 and need to be protected from the Rule 5 draft on the 40 man roster.
2. It means end of the World Series. You can do your roster juggling through Game 3 of the WS; but be warned that the moment the WS is over, so is all "roster juggling" until budgets are set next season.