Here's something better than 'lists'...
Rick:First, it sounds like your friend needs to take a deep breath, recognize that he'll never finish his 'To Do' list, and that he needs to take first things first. Perhaps as a friend, you can coach him a bit in this direction, as both going offshore and going foreign are big events, full of unique logistics issues, and deserving of his focus.Second, here are a couple of references he'll find very educational...but only if he gives them some time & reflection:1. Offshore Sailing by Bill Seifert: new in 2002, it takes many important prep details past the ID stage to actually show how they can be executed, and he's cruised extensively in Europe and describes many solutions to some of the puzzles your friend will find there.2. searoom.com's web site offers the complete set of VELEDA IV's logs as she crossed the Atlantic and cruises Europe and now the Med; this is not only a travelogue but a thorough, frank discussion of lessons learned. To date, it's the best single reference I've found on the web of what cruising there must be like in that region; numerous links also are offered.3. SSCA's latest CD: a compilation of 1995-2002 SSCA Bulletins and offering discrete search capabilities via Adobe Acrobat, there's a huge treasure of info on routing choices, Euro details like VAT, and much more. The value of this info source is that it can be easily accessed as the trip unfolds, prepping further before each leg. As just one example, routing across the Caribbean, W to E e.g., takes some thoughtful planning or an immense amount of bashing to windward. He'll find multiple ways to skin the cat and what to expect with each step.It seems the universal infliction that we all get so caught up in our boat's systems (the trees) that we forget about the forrest (the voyage). Do your friend a favor and remind him that his cruise has, in fact, already begun: the balancing act between boat work, planning the next leg and smelling the roses is constant. Perhaps it's time for him to regroup a bit. And also to leave - soon. He's got a lot of rose-smelling to accomplish along his route before the storm season looms over the Eastern horizon in the Caribbean in 7 months, unless he's choosing to stay put for a half-year somewhere along the way.Jack