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It can be done, but yes it's tough to manage the lines in a small boat.
This is the Federalist and is 15' on deck with a 5' beam, built originally in the early 1800's (this is a reproduction). She sails and is as traditional as it gets. She carries 7 sails, only 2 fore and aft. You can reach up and reef by hand and you can lower the tops from deck by pulling the wedge. Braces and sheets are easily handled, but it is a cramped and complex thing at first glance. There's a few thwarts, but not much room to move around.
All in all a well thought out little ship, but ungodly impractical. If she was slightly larger, say 20', you might have some room to place a cooler full of beer. I'd love to get a commission for something like this, because it has so many issues to figure out.
There are actually groups of folks with interest in these miniature puppies. In England this seems more common, but the USA has it's share. There was this outfit call "little ships", but I haven't heard from them in a few years.
Don't give up your dream, look around - you're not the only nut job () with a vision like this. Go for it.
The Federalist was a gift, in the late 1700's and no intent was offered, in regard to training or as a scale version of something. It was commissioned by some businessmen in Baltimore and presented to George Washington, after Maryland signed the constitution. It was sailed by the commodore of the US Navy to Washington in 1788. She was lost in a hurricane about a month later.
This version is a copy based on builder and designer's notes of the era and was given to the state in 1988. She was designed by Mel Smith (Lynx and Kalmar Nyckel designer) and built by Allen Rawl (currently building a colonial Brigantine, previously built the Susan Constant and Kalmar Nyckle).
The Federalist is sail only, being a historically accurate reproduction. I'd guess it displaces a good ton, with built down sections and a wholesome midsection. Her bilges are pretty firm for a boat of this era, understandably, seeing as she's very shoal. I don't remember seeing a board in her, but she does have a false transom, behind which the rudder stock comes up. I haven't seen her since last year when I was in BWI, but I take note of her when I can.
She'd make a good bit of leeway to windward with her underbelly, but I'll bet she can hang on better than you'd think. Her oar locks would probably be helpful at times.