My boat is the perfect example. It's a labor intensive sailboat, originally rigged. Today we take furlers for granted, but they were a major sore point for old salts, in the day.
Now, just taking some of the labor out of handling the main has a huge effect. And having seen the state of the art in Leasure furl, in action a week ago, we'll be seeing more of that technololgy in the future. My next best thing is to improve the mainsail handling tools, a two speed halyard winch, new sheets, better cover, etc. Stuff like new navigation tools have helped improve sailing as well, at least for me.
Today's new(er) sailboats are easier to sail, that's their mantra. Luckily, many of the improvements can be applied to older boats like mine.