Only have experience on larger yachts. But we always spoke directly with the skipper in advance, generally a number of emails and a phone-chat where possible. Before committing to the charter.

For us it was as important as the boat itself. Sub 100ft with say 3 crew (Inc skipper) they can make or break the holiday.

We were possibly unusual guests on these boats as we wanted to sail it! Rather than just sit and be served cocktails for a week. In most cases this required permission of the yacht's owner. But having cleared all of these things up in advance we always had superb charters and were not difficult guests.

With smaller boats and just 1 paid crew (skipper), with Moorings etc I'm guessing it's quite difficult to speak with them in advance. But, surely, as soon as you arrive you can sit down (maybe not everyone) with him/her and quietly talk through what you want from them and how you want the charter to go. If there is an immediate clash of personalities / you can tell that this isn't someone who is going to make your charter amazing then I doubt it would be hard to talk to management and make a change...

Our experience with Sunsail/Moorings is that it's far easier to get stuff changed/sorted/fixed whilst on the dock. Than to just crack on and hope things will be ok. Our experience is also that in some cases you need to make your case in a more 'robust' manner...after which, stuff gets done!

You can always ask to speak to base manager. From whom you will get more of the 'customer is always right' attitude than perhaps you do with some of the employees lower down the ladder.

Oh and if you want a rum-loving American skipper full to the brim with salty stories, with a great 'can-do' attitude then ask in advance for Captain Lou! They may have to drag him out of the bar, but he's good value! He did our last couple of check-out briefings and we got on very well with him. Knows his stuff and read us very well and got stuff fixed by calling his 'mates' rather than going through the normal chain and got us off the dock in record time.