Here's my 2 cents...
1. Its relatively easy to upgrade a bathroom or kitchen. Heck with a bit of money you can pretty easily double the size of your cottage. But you can never really upgrade your waterfront or location (with the exception of maybe a perched beach). Make absolutely certain that you like your exposure, your part of the lake, your view, your water depth and your lake bottom.
2. I want to echo what everyone is saying about associations. We've had several Winni homes with owned water frontage and I couldn't imagine sharing with anyone. Then we decided to buy on Squam where we could only afford shared waterfront. Its been the best lake property we've ever had. Our kids do love having other kids around but its also the neighbor camaraderie. It helps to have extra hands when its time to put in docks, fix mooring chains, repair drainage issues, borrow a wine opener etc. I wish we had explored an association sooner!
3. Definitely explore the other lakes. After a lifetime on Winni we realized that what we enjoyed most didn't involve our big boat. It was kayaking, sailing, canoeing, longer distance swimming, SUPs etc. At least in our area of Winni it was becoming really hard for our kids to do this with all the traffic and boat related chop. As much as we miss Winni I definitely don't miss the chuckleheads in the 30 foot boat passing 80 feet from my kayak at full throttle!
4. Enjoy the search process! I've found the process of finding a property can be almost as much fun as owning the property!
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