I have had a M-15 and currently sail a M-17 tall rig - Rigging does take some time but mine is complicated by a goofy owner. I store it mast-up dry storage at this time. Between the two boats I strongly prefer the 17 and if/when I change to a smaller lighter boat it will be a Sage 17. Smaller, easier rig, easier to the step the mast, and lighter but 'stiffer' boat when sailing. You really have to sail the boat to get a feeling for the stability of the boat! Faster than a M-17 and a lot faster than a M-15. Okay - you say who cares about speed - if you are trying to outrun bad weather or get to the destination before dark - speed is your friend - you can ALWAYS 'throttle' back - but be honest fast is mo' fun than slow. The Sage 17 is smaller - albeit a couple of inches shorter, lighter, roomier interior and the cockpit is bigger than a M-15 and a bit smaller than a M-17. Easier to rig and can probably use a roller furler that does not use a rigid foil for ease of rigging. Truth be known, I am a fan of Lyle Hess' designs and Jerry Montgomery's boats - ( I am proud to call Jerry a personal friend for years - many of us are his friend and if not you are not yet, you will be!) Maybe I just follow his boats around but I have owned too many GOOD boats to keep track of, and the favorites are his boats at this time. The M-17 should not take as long as a C-22 to rig and most people get them (C-22s) done in 45+- minutes. The time spent rigging and de-rigging is part of the price we pay for sailing - No worn out engines, minimal fuel costs and the experience of sailing. We have become a society of "Instant" and this sport is NOT instant. Okay - Possibly Useful ideas - some are reiterated- 1- Shrouds and backstay to remain attached. 2- Adjustable mast carrier at the transom to assist in stepping mast. 3- Use a halyard to help raise the mast - (See M-26 gin pole set-up for more complication) 3a- If you have a furler with a rigid foil see above comment in brackets) 4- Practice will increase your organization and allow you time to check all before launch. 5- Launching a M-17 is a breeze with anything BUT a SMALL vehicle - If needed add a tongue ext. 6- Good keel guides make retrieving a breeze - but they must be properly set-up.(as close to the bottom of the boat as possible and 'tight' on the sides of the keel) 7- Your boat -Stowing, Towing, Storing, Rigging skills will become more efficient with practice. I personally think selling the boat is a bit of overkill unless it was an A-23 or similar (sorry) The M-17 is a GREAT boat - If easier rigging is desired - Check out a Sage 17 - it has addressed these items and you get some improvements over the M-17 - shoot - look at the Designer - he is a true GEEZER ! It is his choice of boats for his Golden Years! I have no financial interest in the Sage 17 - I do respect and like the Designer, Company Owners, and the BOAT. I have sailed it, and If I changed boats for "age-related reasons" or ease of set-up, I would be choosing my Hull/Deck colors for my Sage 17 right now. It may happen someday. Why am I talking up a Sage on the Montgomery list? - it is one Jerry M's Kids ! That is my opinion - and it's right! GO Take Care, Have Fun, Go Sail M-17, M-7.11, Penguin, Sunfish......... PS - I have plenty of physical limitations to make me 'take it easy'- some self-induced, they have not prevented me from dealing with the larger boat. Use your head -not your ,arms, back, legs, etc..How is that for a rambling tirade doctor???