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Understood about the toy guns. I'd rather have a hammer than a gun that won't fire - toy or real. Contrary to the movies, pointing a firearm at someone does not cause them to freeze. They will charge at you or run - and will charge at you as often as run from you. Rather have a hammer than a knife too. A couple of 12 ga. flare guns could do some damage and might end-run around a no-firearms rule (or might be considered a firearm other places).
I was serious in my view of cheap, throw away firearms if necessary for personal safety as an option of traveling dangerous waters but also where you firearms are prohibited (or you are unsure if they are legal.) I have quietly slipped a few (very few) old rifles and shotguns over the opposite side rather than address the issue. For example, if you are traveling through a national or state park waterway, is there some risk in having firearms as many prohibit firearms in the park? I'll throw away a hundred or two dollars to avoid the question.
Though this many years ago (two decades), in foreign waters I would grease them up and drop them over in shallow water before entering the port, leaving a small float (large bobber) with a line down to them. When departing, would then dive down and retrieve them (couldn't find the location once). The cost of that old rifle and shotgun combined was less than $150 plus $20 in ammo in zip lock bags. I'd rather just toss that much money than cross my fingers and hope I'm up on the local laws of the hour for every jurisdiction I go through and everywhere I might anchor or dock.
On insurance, insuring a wooden boat for lose of or damage to the boat is nearly impossible anyway unless surveyed as truly pristine and generally as the result of work and routine maintenance done by a yard. That is one of the numerous reasons why they are generally cheap and usually sell for less than the sum of their parts if dismantled and sold for parts. Though wooden yachts are more demanding (much) of attention, they also offer much in the way of customizing and brightwork.
Fortunately I like wooden boats, which also then allows us to afford sizes we otherwise could not and a Trumpy is not a Chris Craft woodie. Less than 500 Trumpys were ever made across 6 decades and less than 100 remain, so they are obscure collectables that also are functional.
My post was mostly self pondering of what direction I'm headed in yachting as I enter semi-retirement. One large yacht might make more sense than 2 or 3 medium to small size ones, particularly since we are about decided to shift to primarily a liveaboard lifestyle. However with fuel costs going as they are, keeping the twin inboard 27' cruiser that we can tow might make sense as an option for short term, distance "coastal cruising."
The cost of towing a boat from Florida to New England is much less than travel by water and also allows covering distance quickly for shorter time period adventures. The 27 footer is fiberglass cabin cruiser but with a fine full mahogany interior - an older twin inboard/outboard Chaparall, which are a cut above Bayliners (not to hurt anyone's feelings who owns a Bayliner.)
I tend to disregard regulations instead to decide upon what I want/need and generally get away with it. If I'm in another state and feel like fishing, I will. If
I see a boat is approaching that might be DNR I'll quietly slip the pole off the side if I'm unsure if my fishing license for that state is expired. But a requirement for someone to be licensed is not one I could get away with, particularly on the inner coast, the Keys and offshore from the lower East Florida coast.
I just seemed to remember there was an 85 or 100 foot limit, but not sure where I got that from. I had spent some time looking at USCG website material, but wasn't finding an answer. Looking around further, it appears the USCG allows up to 164' if strictly for recreational/personal use.
Thanks for your time replying.
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