I've been absent for a bit so some responses without quoting the posts.
Credit rating. Insurance companies know, whether car or home, that people with low credit scores have more claims and smaller deductibles which are expensive to administer. Same applies in a recession.
Pictures: In the latter part of my career in insurance sales, I had to take a picture . Same with certain breeds of dogs. If it was out of state, a contractor took pictures. Not a company employee, so s/he couldn't speak for the company, and wanted to spend as little time as possible on each site, not chat with the homeowner.
Reading the policy: There are 3-4 parts to a policy. What's covered, what's excluded, conditions and endorsements. Inter-related, but not in a way that's easy to read. That's why insurance employees are licensed and pass routine, repeated, tests.
Is real estate an investment? To me, only a little bit. It's very difficult to make money if you only have one single family property. Even harder if it is seasonal. However, taxes, interest, management fees, etc. are all deductible. Along with depreciation, you can shelter a good part of other income. You can deduct travel expenses to inspect and work with your manger, etc. This could be in nearby Laconia, St. Thomas or St Augustine, within IRS limits.
At this point you have to be operating a business, not just keeping the family camp, in the operating methodology.
Family Camp Investment Fund: If an older generation established this and it has a lot of CD's or other fixed income "to be safe" you're losing money from the start as you just barely keep up with inflation. Instead of a 10 year horizon for retirement, think of a 50 year horizon for two generations beyond yourself. If you have no knowledge/experience, you can do index ETF's at very low cost with Vanguard, Fidelity or Schwab. A fee based CFP can help but be cautious with an advisor who charges a percent based on the size of the portfolio.
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