Planning on Sailing TI from San Diego to the Panama Canal

Right there, you mention what I believe is your MAJOR folly. You speak of beaching your yet to be purchase TI in swells....

These vessels are DISASTROUS landing in swells, according to almost all reports I have read here. It would seem that almost the only safe way to land an Island in any sized shore break is to raise centreboard and rudder, tie everything down, and then go overboard attached to the bow by a line a couple of boatlengths long (so you are a few waves back). You then act as a drogue chute, helping to avoid the vessel being turned sideways. You then land it backwards.

If arriving in the breakers facing forwards, there is a huge chance that the rudder will at some point be out of the water, making it very easy for the stern to swing sideways. At that point, one ama is likely to be buried down in the wave, leading to any combination of akas being destroyed or capsize with serious potential for damage to the mast. Imagine then being stranded on a possibly remote beach, with a vessel too crippled to continue (I could not imagine that your spare parts inventory could be comprehensive enough to include at least two (but preferably more) spare akas, or even, god forbid, a spare mast as well)

Please do not think I am being over dramatic here... With luck, you might even be able to find the video which was posted here, which showed the spectacular consequences of getting it wrong.

My point is that beaching an Island is absolutely nothing like beaching a single hulled kayak (and even then, you can find literally thousands of reports of single-hulled kayaks being rolled in the surf).

As has been pointed out above, a mammoth trip like yours is going to involve at least about 100 landings. Given the above dangers of surf landings, I believe that you would be prudent to plan for ZERO surf landings, on the basis that the probability of a disaster befalling you is simply too great to rely on such landings, in anything but an emergency situation. Of course there would be times when conditions are moderate enough for landing on a beach, but treating those occasions as unplanned bonuses would be the best way to consider them.

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Tony Stott
2012 Tandem Island "SIC EM" with Hobie spinnaker

Please tell me your going to use the pedals at least???? A TI w/amas is NOT a good paddle yak. You will bust it up in the surf landings at some point, guaranteed. And if you leave the amas/akas off, you will roll it while sailing and or surf. Go with the Hobie Oasis Tandem if your intention is to sail and paddle only. You can use the small sail on the Oasis. Figure out a way to secure it to the kayak so that when you do roll in the surf, you don't lose it. If you plan for the occasional rolling then you could make it in say a year + on an Oasis???
On a TI,
No motor + No pedals = No making it
please let me know when the bookies in Vegas are ready to give odds.

EDIT: I think you have the wrong kayak design/designer for your intentions. Get a VERY good tandem paddle yak (SIC) that can be modified for an additional small sail.
Something like this on a good touring kayak, http://www.pacificaction.com/
Not as glorious but far more effective and fool proof for the job at hand with your given handicap to copy history.

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Mark
Tandem Island- 2013
2 - Sports - 2014