Sorry about the late response. I've been away for a week.
Yes, I did drain all the fluid and I also ran the fresh stuff through it while warming up the engine to change the oil.
Seeing as the marina replaced all of the bellows last year, I am going to have them look at it - give it a pressure test, etc. I notified them and hopefully they'll get to it soon. They still have a few other boats to winterize.
In regards to the drive cooler, yes I added a Simrek, because at the end of my short season(s) ( I said black before and may be a little harsh) the lube was extremely dark. I do not have any white build up though. As I mentioned earlier, I do spend a fair amount of time on plane hopping from islands, so I put one on erring on the side of caution.