Best bet is to go with a larger carrier, that way you have no worries about crossing state lines or going into Canada, although you if you venture into Canada it'd be advisable to check with your insurance company to be sure they will cover you up there. Theft is a HUGE problem in Canada.
I have full coverage on both my machines via State Farm with $100.00 deductibles on each. Cost is $100 and $106 per sled per year respectively. That's for identical coverage as posted for Allstate earlier.
Even your sea doo coverage seems pretty high. I'd consider getting a quote for that if your in the process of shopping around.
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