Been there, done that
The question is not the size of your driveway, but the size of your available free time. Driveway storage commits you to raise and lower the mast for every sail, and to stow the boat and trailer for highway travel. On most boats the time you will spend doing that will be at least 75 to 90 minutes per outing.Contrast that to the two other alternatives:In a dry storage lot at your lake, the mast can be left up and the mainsail can remain on the boom. You can launch and recover the boat without ever having to put up and take down the rigging, saving those 90 minutes or so.In a marina slip, you get all of those advantages, plus the additional one of eliminating the launching and recovery time. A slip also allows you a chance to socialize with other boaters, to stay on the boat overnight, and so on.You get what you pay for in these choices.