I honestly think it all comes down to money for Oxboy if he wants a job "on the water".
The harsh truth is as follows:-
a) In the UK there will be several months of the year when you cannot get out on the water at all. So that means no income if you are self-employed and dependant on skippering/instructing for a living.
b) As and when you do get out in the nicer months, you will do well to get £100 for each day you work.
And its not as if there are big bucks on offer from Sailing Schools as permanent employees. Most adverts I see for instructors are with salaries below £20k.
But - I have to say that getting the Instructor and Yachtmaster Commercial rating was probably the best thing I have ever done from a point of view of getting enjoyable part-time employment!!
There's the rub...........