My 24 footer is too much work to raise and lower the mast for daysailing. It takes about 2-3 hours to raise the mast and run all the lines and bend the main on. It takes three hours to put it away for a road trip. It's a high performance boat with lots of lines everywhere for codes zero, spinnaker, main and jib.
For daysailing, I either keep it in mast up dry storage on the trailer or a wet slip. I now single hand alot because my husband travels for work, so I prefer a wet slip. But I've had wet slips and "dry slips" with mast up storage at various times over the past 30 years. Many yacht clubs have a crane for launching boats. Many marinas also offer crane launching or mast up ramp accessibility.
There are some attractive features to dry storage with the mast up. If my hubby and I were both retired, we could save $3500 per year keeping it in dry storage with the mast up. it saves thousands of dollars per year in slip fees, bottom jobs and diver. And there is far less rusting and mold etc to worry about. Dry storage is kinder to the boat. As for the hassle factor, launching by ramp or crane is an extra 15 minutes max once you get the routine down.
Around here, a 28 foot wet slip costs at least $150/month more than a comparable dry space on the trailer with the mast up. Dry storage also saves $400 year in diver cost, and about $2000 every other year in bottom paint jobs. That's $3400 per year.
Judy B