As I posted earlier, you test in increasingly heavy conditions.
Start taking the boat out when it is blowing. When you are comfortable with all of the weather that will still allow leaving and coming back into port, you can step up.
Leave a day or two before the passage of a front to gain sea room, and negotiate the heavy weather to test your systems fairly near shore. Safety and help are not far away if something huge fails.
How is this simple, time tested procedure nonsensical? Do you believe you can only shakedown in nice weather hopping down the coast?
Airplanes, cars, and just about anything are tested gradually in this same manner. Look up sea trials, and see that most passenger ships are given trials in progressive weather up to what is expected routinely before they ever carry passengers.
The idea that most people don't do a proper shakedown somehow makes it seaman like is certainly nonsensical. Seamanship is not democratic, it is tried and true methods for surviving the unfathomable power of the sea. The rules of seamanship have been developed by analyzing and learning from the failures of ships that are lost, and the methods of those that have thrived, over hundreds of years of history at sea. Basic rule of seamanship; watertight integrity. Ranks pretty high.
Nobody here pulled any punches discussing the Bounty's very poor watertight integrity, it's deceased Captain was held feet to the fire right here, because the boat should have been fixed.
Modern people are way too smart I guess to do things the right (hard) way, and don't have time for all of that. Besides they have satphones and spots and inreach and epirbs and someone else can always risk their life to come get them, so just do it!
No time to fix the boat, learn the boat, or do a shakedown, just go!
The Pardey's have sailed all of their miles without any of these "safety" gadgets, taking the ultimate responsibility for their own safety at sea. I can't imagine Larry leaving port with a rotten boat, because he knows no one will be coming to get them. They always stress learning your boat in increasing weather conditions until you are comfortable in the snot, but what do they know, they don't even use a gps or a satphone.
So rather than fix the boat, make sure your sim cards are in order, and head out! No big deal to have someone else's kid jump into the ocean and risk their life to save you, it's their job.
Yes, me, the Pardy's and the very rules of seamanship are nonsensical, who needs that crap. Finding out what will surely break should be done as far from land as possible, preferably with precious cargo. It makes for a much cooler book.
Highwire artists should all begin learning 100' off the ground! Shakedown shmakedown. Ainobody got time fuhdat!