OK, my two cents worth. I live twenty miles west of Chicago. Last season I trailered my boat to/sailed her on: Illinois river, Winthrop Harbor (IL, Lake Michican) many times, Lake Muskegan (MI, Lake Michigan) many times, Clear Lake, MI, Mississippi river, Columbia river (OR) and the San Juans (Whidbey NAS, WA). I love doing little treks and probably sailed more than 75 days total. I love looking at the NOA weather reports for my area and going where the wind blows right.... for me. An hour at the front and end of each adventure was well worth it! I stay on my boat as many nights as I can... til the frost drives me off in the fall. EVERTHING is a tradeoff, don't kid yourself. Figure out what you want that trailer for and go for it! I lived 3 years in Alaska once. A friend confided to me, "If you come to Alaska and want to have a good time, you can't be cheap-skate." There is sailing and then there is SAILING. Take your pick and try it. It's OK to change your mind.. at least you tried!