Some more considerations
Mandolin player and kitesurfer, you might be an alright guy.
I still think you should by a smaller boat to sail while you figure out what exactly you want in a 40+ foot cruiser. Get a good deal on a small boat and it won't be too hard to sell at a slight loss with a lot of learning and sailing in the mean time. In the mean time you can take your time to study up on bigger boats and choose the right type and the right boat. I have never owned a boat bigger than 22 feet but have spent 20 years sailing off and on and racing other peoples boats, hanging out at the marina and reading tons of stuff on sailing. I would not know what kind of boat to choose in this range as I have never aspired to anything bigger than 38 feet. I have read plenty of stories of people haven taken on too much boat and not ever leave on their trip or running into too many issues to make the trip enjoyable. As Xort pointed out a newbie can make a good first go at sailing a big boat. He did however take 2 years to figure out which boat he wanted and still contemplates the compromises he had to make.
I am not sure of your location and setup but it does not make sense to me to limit your boat's draft or mast height just to have it a few blocks from your house, when the long term goal is to take cruise it long distances. I would opt to have my boat and condo on the other side of the bridge if that is where the sailing is to occur. I would rather spend 20 minutes driving to my boat than 1 hour motoring the boat to the sailing area. You will get more sailing in that way.
Walk the docks and look at the boats you like. Maybe spend weekends scoping out the marina and if you find an owner on his boat they will most likely be willing to show you around and talk to you all day long about their boats.
West Wight Potter 14 "Lemon Drop"
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