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Breaking things down point by point:

-- Did the use of the crane contribute to your nervousness? I can see that being a pain, but it's different from the actual sailing part. I infer that your friend not an experienced sailor. It might be worth it for both of you to go out with a more experienced sailor a few times. Help them launch and recover their boat. The whole experience should get easier with practice.

-- When you ask the order that sails "go on", do you mean installing them on the boat, or raising them? It's usually easiest to raise the main first, but there may be situations where you do the opposite. If you are talking about "installing" them in the first place, it shouldn't really matter. (I assume the sails are not stored in place.)

-- I don't understand how not having a backstay is relevant. (Don't J22's usually have a backstay?) I assume you are talking not having an outboard motor?

-- Whether you can safely sail through a channel depends on lots of factors like the wind, obstructions, etc. We would need a lot more detail to judge that. Raising the jib will not only give you more power, it will let the boat point better (that is, sail closer to the wind.) If the channel is upwind, that might help. OTOH, having the jib up gives you one more thing to worry about when maneuvering. It might be too much sail for the windy conditions. Does your friend have a smaller jib? You might also consider reefing the mainsail.

-- Getting wet on the foredeck of a small racing boat is part of the experience. Doing it in high wind without a lifejacket is _not_. On that sort of boat, you really should wear one all the time, and not even think about going out without one in the conditions you describe. Most of the other things you mention are of the sort that you might laugh about later. This mistake is the sort that gets people killed.
 
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