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I installed a traveller just forward of the cockpit lockers. It works great,. But... Its a bit of a hassle to step over all the time. It reduces seating. Two spots available rather than three. When you are off the wind then the sheet gets in the way of the forward lee seat unless the traveller car is eased to lee. These problems are not a big issue to me since I am single handed, but I you are two people then they become an issue and if you are three or more then it is a huge hassle.

The corner of my asymetric clips onto the shroud and a rope goes down to a pulley on the stemhead and then back to the cockpit so the height of the tack can be adjusted.

The English Contessa has a boom that is longer and a mast that is shorter than the Canadian Contessa.

One advantage would to be able to open them up to inspect for rust every few years. I had a shroud that started breaking strands at sea, even though there were no signs of rust from outside of the swag.  After it was replaced, destructive testing showed that there was sever rust damage down inside the swag. They were 25 years old with some salt water years.

If you are unsure of the strength, you could add an additional beam under the mast step. I added a beam to mine. See pic. It is a laminated oak beam Approx 2" x 2". It is bolted from the aft side through the glass beam, the plywood bulkhead and through the oak beam. You can see some of the black bolt heads in the pic. Someone else has added some pics of a similar installation showing the forward side. Do a search for "beam" in the galley section. Before the beam, the rigging would be loose after the first time sailing in hard conditions each year due to the roof sagging. My setup has two transatlantic crossings on it without a problem.

Dzus fasteners are available at Aircraft Spruce and Specialty. The have an outlet in Ontario. They will sell in much smaller quantities.

If you are cruising, I would suggest an automatic electric eye switch for the anchor light. It was common for me to go away from the boat in the afternoon with full intent on getting back to the boat before dark and then before you know it, its 10pm and you are still sitting on someones boat or restaurant. On one occasion I went to a beach party with only my prescription sunglasses. On heading home in the dark, I ended up motoring around the crowded anchorage. I could not make out my boat with the dark glasses on and I could see any boat with the glasses off.

I know lots of people who have brought US boats into Canada. Very easy. Most cross border transactions are similiar between the two countries. Should be able to find out with a call to your favour customs bureaucrat and boat licensing office.

I have 3 reefs in my main with permanently rigged reefing lines to the cockpit. I perfer this over the tri sail. The main thing to remember is that with any solution you will be rigging it in storm conditions. Dragging a sail on deck and getting the sliders into the track while the rest of the sail is trying to rip out of your hands in 45kts is "problematic". Same with reefing with out all the lines in place ahead of time. I found that sailing very close hauled ( almost zero headway) with a storm jib only was better that heaving-to. After that a sea-anchor worked great when the sea was too large. (if you have sea room)

expanding liquid foam is a two part liquid like expoxy. You quickly mix the two parts together and it starts expanding into the cavity. I am not sure how the R value compares to rigid boards designed specifically for insulation. One other factor to consider on a long voyage is that ice is hard to find in many areas or very expensive. I started my year long trip with an ice box and half way through converted it to electric. The frig0boat units are very efficient. I only had a solar panel for power. I paid $9 a block for ice in Bermuda. In the Azores it was unavailable except at the fish plant for free at a particular time if you were lucky and after a mile walk. I eventually gave up on ice.