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Soukus,
I have never been boating on the Great lakes so I can not speak directly to costs and such in that area. But one thing I would say is buying a used boat from that area is probably a far safer bet then in most places. First it is fresh water so corrosion to the engines and systems should be minimal if the boat was taken care of. Corrosion is by far the most damaging to a boat. Secondly, I think over all the boats aren't subjected to weather as harsh as the East Coast or the South so the hull and top sides should not need extended refurbishing. Third The season is probably far shorter due to weather so the time a boat spends being used is probably many hours less then in other areas. I would think that a 10 year old boat may only show the wear of a 5 year old boat from another region.
I grew up in Wildwood, NJ a barrier Island about 30 minutes south of Atlantic City. I have been on boats my whole life. I have sailed the entire East Coast in all size boats and slept on many for extended periods, some as small as 20'.
A newer 30 foot power boat (not a sail boat) makes for a nice family weekender with most if not all of the amenities of home. Bathroom (head) with shower, kitchen (galley) with stove, fridge, microwave, sink H/C water. Dinette, A/C and heat. TV, DVD, Stereo etc. Storage for clothes, towels, toiletries, etc. A 30' boat will sleep 4 in relative comfort.
As for winter storage a 30' express style boat is easily trailer-able with a 3/4 ton pickup, suburban or the like. So if your HOA, town or municipality allows it you can block it right in your yard. This would allow spring commissioning and fall decommissioning to be done at your home where you have everything you need. As well as updates or repairs you may want to make. Most gas marine engines are based on car engines. Maintenance is relatively the same on the engines as with the car version just more often due to the increased loads being placed on the engines.
Sail boats are great fun but far more work then power boats (more work means less play) and have far less room in the same length. Sail boat hulls are designed for efficiency to move through the water. So a 30' sail boat may only have the interior space of a 20' power boat and less amenities. Like no A/C
As for docking keep in mind boat slips are generally rented based on a per foot basis with slips going up in length 5' at a time. So if you buy a 31' boat you may get bumped up to a 35' slip. Also at about 30' the width (beam) will start to get wider. A 29' are about 8' wide. A 30' boat will be about 10' and maybe 12', again moving you into a bigger slip. Also if you do intend to trailer most cabin cruiser style boats will be out of the question as they will exceed the 14' height allowed on roads and highways with out a permit. Sail boats and cabin cruisers will also limit your access to many areas when on the water.
Although I have a passion for old wood boats fiberglass is the way to go.
Just like buying a used Pcar invest in a PPI (survey). Even some of the good boats go bad and some of the bad ones are good.
Lastly, unlike a house a boat even what some would consider a big boat (30'-40') can be trailered as I said above. You can take it from time to time to other areas and put it in the water and explore. I have many friends with motor homes but their stories and adventures never seem to match our stories and adventures.
Living aboard is a great way to spend time with the family and meet new people. I guarantee your children and you will go away with experiences they and you will treasure forever. The two best days of owning a boat don't have to be the day you buy it and the day you sell it. Some of my worst days were the days I sold my boat and didn't have one for a while. There is nothing like being on the water.
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