Sorry for the tone of some of my posts and would agree that the thread has changed plot considerably.
I know that long distance trips are common down south, but also note that the practice of small boat owners clubs is far more common than up here and group outings are far more common. The seas are also far busier so help is likely to be much closer to hand.
With regard to charter boats breaking down I would suggest this is more a case of the law of averages says if you go out to sea every day you are far more likely to have some kind of problem than the guy who goes out a few times a month.
I have not spent a lot of time on charter boats however on the 5 occasions I have been out to "the wall" ( which equates to about 280 miles of steaming) the skipper has always teamed up with another boat rather than go it alone. A sensible precation taken by professionals who know they have 2 1/2 hours steaming each way.
With regard to the 22 footer that was swamped at Whitby, you ask why did no one stop him going out? My own experiences of that are port are as follows.
I have my new boat, first trip planned to Whitby. We arrive at the slipway, go in the harbour masters office and pay our slipway fee and parking ticket. Buy the bait and just as we are backing down the slipway a local tells us we have no chance of getting out of the harbour mouth. A quick drive down to the seafront confirms this to be the case.
Back to the harbour masters office for a refund...no chance..
Why did he not tell us it was too rough before we payed..."Not my job"...which to me roughly translates to "I've got your money and I dont give a ...."
Hardly the attitude of a person you would expect to call you on the radio if you were heading into danger.
Theres a nice link here for the Sheltie and one owners modification list to make it more suitable and safer.
Shetland Owners Association
I was under the impression all shetlands were twin skinned with a foam infill to make them unsinkable, seems that is not the case.
If this summer was anything to go by your chances of making a 40 mile trip are pretty slim.
Cheers
Dave