Advice Wanted - Sell the Lakefront House or Keep it in the Family?

[Descant]

Many good insights here. What I don't see is any consideration of grandchildren or great grandchildren. My father asked everybody about keeping the camp. His children and grandchildren, noting that at that point, one grandchild was only 6. But he had seen and we have seen many many families sell and only a few years later regretting that they didn't make every effort to keep the place until the next generation could afford it. We can all think of good money management plans that will make it possible to afford the place, especially since there is no mortgage.
Some history, as just one example.
In 1986, we established a realty trust with 5 shareholders. Three of them were grandchildren, to under 18. There was no money in the trust, but Dad paid the taxes and the rest was DIY. In 1991, he and my mother did some more estate planning, again establishing unfunded trusts for future needs. While they were in Florida that winter, they decided to move to a retirement community in NH which we arranged. As they were moving, they established NH residence. Dad died unexpectedly, but as a NH resident, even for only a few days, he and Mom saved a bundle in Massachusetts estate taxes. Over the next 35 years we funded the trusts, having sold the Massachusetts house, and retirement savings for example. Each year everybody involved as heirs got an annual stipend and a little went into the original realty trust. These were "gifts", so no income tax. The kids' money went towards "education", but not necessarily college tuition. Note that if you have large sums of money in the wrong name you may not be eligible for some scholarships or other tuition aid. Two of the original five shareholders didn't have a lot of interest in camp, but no problem, since nobody was asking them for money. My sister gave her shares to her granddaughter, moving things along to the next generation. Just a simple letter of transfer.
I know that was somewhat lengthy, but the point is, if you can see how it works, you may see how something might work for your family.
Key points:
Estate planning is very important
Establishing residence in Boston, MA can be hazardous to your financial
health
Regardless of where you live, a NH Trust does not pay NH Interest and
Dividends tax
Taking money in large lumps almost always incurs large taxes, at higher tax
rates

Aside: Spending 6 weeks at camp is a dream for thousands of folks who only get to do weekends. College tuition saving is way overrated. Your kids will go to college one way or another. They may never again have a place on Lake Wiinipesaukee.