1. The first cycle after 24 hours of acceptance. R5 changes things. If it doesn't process before the R5, get a Snickers.
2. Yes. I'm not sure it's needed in HBD as you have 10 years no matter what. 3 min, 2 arb, 5 LT. With development/decline pretty standard, position players are in decline between 30-33. Pitchers hang on a little longer.