The biggest thing you need to worry about is your banking deadline date, assuming you have unused points or didn't use any points at all in a UY. I would just put a calendar reminder a week before or so each year.
Absolutely. We have 3 resorts w/different use years, so it helps a lot. It also allows me to try out hypotheticals. "If we spend these points here, where does that leave us for the next year," etc. I could not manage our points without it.