Sailing is always about some risk, you cannot mitigate all of it. Shat happens; things break; winds can knock you down, winds can disappear;thunderstorms can come up. But going out without proper equipment(like cell phones AND your base VHF AND your portable VHF) is just dumb. But this is all about planning.
But, IMO, winging it is not the way to go. I've always gone with the Eisenhower. You may make plans and then you see what will actually happen.
But you need plans for eventualities, particularly those that are critical. For example, if your only propulsion besides wind dies and won't start, you don't head out into ocean looking for more wind. Thinking ahead tells you that if the wind dies completely you will find yourself becalmed drifting. In that case, you forget about adventure and head for shore. This particular dude(because he was way more experienced that us) forced us out into the deep bay looking for better wind, and then the wind died completely. Eventually the adventure turned into a disaster that required rescue by the COAST Guard, and even that was touch and go since we were out of range of the CG.
Now.... I would not let that happen and we would sail for shore with what little wind we have. Plans for possibilities.
Another possibility which while remote, could be very very difficult to deal with on a little boat is man overboard. It will not be an adventure and fun up here if that happens since the warmest the water ever gets is 55 degrees. That's hyperthermia in a very very short time. And on a little boat, it can be very difficult to get a wet person who has been in the water at 55 degrees for 15 minutes back into the boat. They wont be able to help much. And what is a little swim for a 25 year old, can be seriously life threatening very very fast for a 70 year old. This dude is 76. His wife slipped into the water at the dock and while not life threatening was very scary for her in 55 degree water.
All kinds of pulleys and life lines are possible, but the easiest is actually a 2 ton hand winch connected to the baby stays. With a wide banded sling, you just crank them up to the gunwale.
And the added benefit is that if you can't get your 400 lb dagger board up at the ramp, a potentially impossible situation, without a lot of fun adventurous options, you can rig the winch to bring it up by-passing the internal winch.
Its always about plans: Sailing plans, overboard plans, launching plans, etc. If you have the plan, then you can implement it, and improvise around it.
If you never made any plan and are just looking for adventure everywhere, then sooner or later you will run into an adventure that scares you shatless. If that's what you want, great. For me, being scared is not part of fun---and scar's are part of scared.
I don't like things that cause scars, healing is always a pain.