Most of the newer boats I see out cruising have mains that roll up in the mast. I don't think I'd like that. Our current boat has lazy jacks that work pretty well but I prefer the Dutchman system on my previous boat. As far as reefing goes, I'd opt for whatever you can set up so that you can reef without leaving the cockpit. That way you're more likely to put in a reef before you come to wish you had earlier. (We have three reefs that all work from the cockpit. I'm no expert on any of this. Just noting what I've come to like. Good luck with the changes.