Which first: dinghy or life raft..

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I suggest you purchase the life raft first. The reason for this is you will quickly, if not sooner, realize you really really need a dingy. I interpret your statement cruising the San Juans to really mean the Gulf Islands and Desolation Sound and Jarvis Inlet as well. If this is the case, for example in Desolation Sound, you'll be on the hook most of the time and won't be able to get off the boat at all unless you have a dinghy.

So by purchasing the life raft first, you very quickly purchase the dinghy second. I'm on Vancouver Island and most larger craft here don't have a life raft but do have a dinghy.
 
Without doubt, the dinghy first for that use.

While a good dinghy will have very little maintenance cost associated with it, a liferaft is entirely different. Most require repacking every 3 years or so, and the repack is very expensive - figure about 1/2 the cost of the raft. You are highly unlikely ever to use it in Puget/Salish. Help will be there before you could get it inflated. If you were planning to go offshore to Mexico, then I'd consider one.
 
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More importantly, who should I vote for - Nixon or Kennedy?
 
I suggest you purchase the life raft first. The reason for this is you will quickly, if not sooner, realize you really really need a dingy. .

Or......Buy a Portland Pudgy with the "Life Raft" canopy. Kill 2 birds with one (several) boat units...
 

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