I've offered to pay the person who watches my dog directly, and she declines exactly because of the value add of Rover insuring her. Seems a fair model.

I thought it was fair until I found out they were taking something like 20% from the sitter on top of charging me a service fee of 5% or so.

This conversation actually made me curious what the actual value of that insurance is.

According to this source, at retail prices dog walking insurance costs 500$ a year for comprehensive coverage, or about 40$ a month: https://www.petsits.com/petsittinginsuranceusa

Rover takes almost 40$ in service fees for one weekend of boarding my single dog!

I appreciate the value of insurance, I kind of appreciate the Craigslist+ role they serve, but at the point where more than 25% of my payment is never making it to the sitter... Rover is just burning my money to fund a bloated payroll and lofty valuations

Doesnt bother me in the slightest. Sitters seem happy and protected, I'm happy and protected, the vendor makes what they can. Not everything needs to be a fight against the injustice of middle-men.

Can you not insure yourself, or insure yourself against someone else?

Businesses can often broker discounted group policies which are a fraction of the cost of what an individual policy costs(e.g. health insurance).

Sure, but Rover is presumably benefiting from a much better economy of scale and bargaining position (since it's buying for however many thousands or millions of users it has), whereas you are unlikely to be able to do the same as an individual.

Yes but at that point and for the price it's a convenience/time thing. I probably spend 250 or 300 a month on dog sitting through Rover. The time it would take for me to find a way to self insur is worth considerably more to me than 300.

We also use Rover because they have insurance that allows the dog sitter to take your pet to the vet and pay the vet for services without you having to be there in person.