To deal with your first point. Granted that singlehanded yachtsmen do sometimes get into difficulties but do you know of any instance where one has shown any expectation that he/she is entitled to be rescued? Certainly they might let it be known that they are in difficulties and be very grateful if someone does help but that's a far cry from expecting help. Also do you know of any instance where some person or organisation has been unwilling to help; most people admire personal courage and are happy to do what they can to foster it.

Secondly, a singlehanded yachtsman in a small boat of the type used in the Jester Challenge offshore poses no measurable risk to anyone else's life or property. In the extremely unlikely event of him/her colliding with another yacht in the open ocean it will probably be going in the same direction, as determined by the wind, so it is only going to be a glancing blow. If he/she collides with a ship or a reef the only person who will suffer is the singlehander.
They also develop an awareness, or sixth sense, of what is going on around them which the molly-coddled majority never experience.

You say you are a "safety professional". You are therefore used to carrying out "risk assessments". Perhaps you would do one for us? I'm not being facetious here; it really would be interesting to have someone look at all the factors involved and tell us how risky offshore single-handed sailing really is to other parties.