Is Crewing Safe?
With the rise of the internet, the interaction of skippers and potential crew has increased dramatically. With it, books have been and will be written detailing excellent adventures and strong friendships forged, as well as the darkest side of a former NBA player''s and crew''s last experience.
Compatibility issues are the same as any involved with personal or business relationships and I will assume you and your wife can deal with that.
Seamanship and boat preparation are probably at the heart of your concerns. Here is where your research should begin. What is the resume of the skipper? Has he successfully integrated unfamaliar/inexperienced crew on like voyages in the past? Is there capable crew in addition to the skipper?
Boat preparation - Had a friend wander down to BVI to hook up with an E-Mail arranged crew assignment and ended up doing an impromptu engine removal and replacement in a secluded cove!! For this, a personal inspection and daysail/short coastal voyage without the time constraints of imminent departure on THE voyage would be advisable. It would also be recommended to start with a series of short coastal cruises in well traveled waters as crew on various vessels anyways. Nothing like hopping on a Hawaiian bound vessel from San Fran on the first cruise!!
In short, a little research beforehand can cut down some of the contingencies. But you are after the adventure??