Generally the point of underwriting is to look at the specific individual and write a policy that accounts for their own particulars. Otherwise nobody would take any policy in any case where they would come out behind, so the insurance pool would be 100% 'adverse selection'. Insurance companies need to come out ahead
on every policy, on average, that's how they're written.
A practical example of this, my insurance company told me to cut down a tree they thought was too close to my house for example (and I agree, it was a pine which tend to blow down, and it was too close), or else it would have affected my rates, and if you have particular high-risk breeds of dogs (dog attacks are covered by insurance) you will pay more as well.
In this case - if you keep making claims against your homeowner's for accidental damage to contents, even via a separate high-value-property rider, that is going to be accounted for the next time your renewals come around. And the next underwriter will be able to see those claims as well, those claims data are shared.
I had a high-value-property policy on a laptop (through USAA) and made a claim, they actually tried to come through to my parent's homeowners' insurance as well (which my parents didn't like and they backed them down lol). USAA is great in general, great about paying up when the bill comes due but, insurance is insurance.
So if you want to be nitpicky - no, they do come out ahead on any specific policy, on average - that is the point of diligence in underwriting, to account for those individual-specific factors. Even if you are "riskier than average", they will eventually account for that too. What is true that once written, they either win or they don't - and some policies they will lose. But the expected net value is biased to the house, on every single policy, given the best information they have.
In economic terms: perhaps there is some alpha that you as an individual can extract with your precise knowledge vs an unaware underwriter - but over time as you exploit that, the alpha will decrease to zero, because it will show up in your claim data. Just like any other market, alpha decreases to zero.
The house always wins in insurance, on average. You're not special, you aren't going to beat the house in the long term. Insurance is a "smoothing" tool, it lets you break a $5k lump expense out into $50/mo payments, it's not free money.