Hi Sullivan, you mentioned Mallorca. I can tell you that yes, yes, yes, there are many boats there that you can make a living on. Many many mega yachts, too. From what I recall
, boat tradesmen were very good at overcharging, too ;-). Guess they were use to the endless budgets of the rich and glam. If you want some of that action, dressing will be important. I wouldn't say long pants etc.; just look smart, clean and respectable.
Although there's dough to be made there, cost of living is high. And as far as free anchorages? I don't know of any but doesn't mean they don't exist. Maybe someone else can chime in here...
Not far from Menorca, one of my favourite spots in the world.
Sounds like a great adventure ahead of you!