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Dusty,
The trip from Panama up the West Coast is a long upwing slog...  As long as you're going offshore on the Atlantic side, do the Pacific side right and go to Hawaii, then run north until you pick up the westerlies to take you home to Alaska.  There's a reason sailing ships did it this way for centuries...  I did a similar trip north to BC about 15 years ago and we were rarely close hauled that whole leg of the trip.  The only danger is that once out in the Pacific, you might like it and head south for the Marquesas instead! 
Bill

John,

The standpipe transducer installation is very common in tugs and other commercial vessels (except that it's usually a steel pipe or box instead of PVC...).  My Alberg 30 has a similar setup and it works great (thanks to the PO).  You can use any stock through-hull transducer with this setup.  It's also easier to service or replace should it fail.

If you go with the "hockey puck" transducer take the time to build a horizontal mounting surface rather than just mounting it flush with the hull.  This can be done using a wedge shaped plastic form as a mold for thickened epoxy (a waxed cottage cheese container works well and removes easily).  Cut it to fit the curve of the hull and seal around the outside of the base to prevent leakage while the epoxy sets up.  You'll get better depth results on both tacks this way.

Bill

One quick test is to puncture one of the larger blisters (be careful of youe eyes, as the fluid can spray out).  If the fluid has a strong vinegar-y smell it indicates osmosis and dissolving resin...  Opening up a few representative larger ones will also give you an idea of their depth.  You can temporarily fill and fair them and sail for the season, now having some knowledge that will help you plan your long term strategy...

John,

Despite the recommendation for 4500 lb breaking strength, I'd stick with 1" 4000 lb rated webbing vs the 2" 6000 lb rating.  The 2" webbing will be very cumbersome in a tether clip, and if it's not easy you won't use it. 

I'm also a certified mountain guide and we use 1" tubular webbing to build anchors that people regularly fall vertically onto with resultant large loads.  The loads you'll see in jacklines should be significantly less in the vast majority of cases.  In addition, the jackline system is only as strong as your attachment points.  Will they hold more than 4000 lbs?  (would you be able to lift your boat on two of them?)  Maybe yes for the bow cleats, maybe no for smaller padeyes...

Remember that many more people go overboard because they lose their balance and stumble, than in big dramatic knockdowns or pitchpoles.  This is mostly what you're trying to prevent.  As long as you buy the good tubular webbing rather than the flat sailtie stuff and remember that nylon breaks down over time from UV exposure and replace it regularly (depending on how many days you're out sailing each year) you'll be fine.

Bill

Thanks for the inquiries...  the sea anchor is spoken for.

... and yes, it comes with the deployable storage bag and the optional trip line and recovery float...

Bill

Interesting idea, but I'd be really leery of mounting the sheet on the gallows.  The leverage up that high would put huge loads on the gallows bases.  An accidental gybe could rip the gallows right off.  I'd run a traveler on the aft deck between the gallows uprights instead.  The other advantage of keeping the sheet down low is you can use the mainsheet to lock the boom down in the gallows when motoring, when tying in a reef, etc.  With the sheet mounted up high on the gallows the boom would be too close to do this - the sheet would be two-blocked before the boom was down...

Remember that your rig is only as strong as it's weakest component.  If you increase the diameter on your standing rigging, make sure you thoroughly inspect the chainplates and the chainplate bolts.  If they're questionable (as many are on older boats) your rigging upsize may not increase your rig strength at all...

Try penetrating oil on the threads, letting it soak in for a week or so.  Then GENTLY tap on the plug to break it free before turning it.  Save heat as a last resort if at all.