We trail and sail our H260 in the San Juans/Gulf Islands almost yearly.
As Dave said - preventative trailer maintenance is key. Do your brakes work? I'm much less concerned about a flat than hubs - the finger test is good but a $20 infrared thermometer provides great data and a base reference.
Re: motor and tidal flows. There are some passes that run too strong for a 9.9. I'm going up to a 15 hp as we had a tow/tide situation a few years back where the Bigfoot was maxed - not fun.
We don't beach (although stern tie a lot in lakes). You will want to look at a heavier anchor and more chain (with the caveat that you are a human windless). Anchorage can get crowded.
The crabbing is good.
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However, there are shipping channels (not close but a cool pick of the H260). A hard wired radio with AIS is handy.
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You will love it!