Originally Posted by DWhylton
You can buy a 2007 boat for the same money or less than a thirty year old private boat. All the electronics will be modern and best of all the boat design will be modern. Obviously you have to do your do diligence get a survey and personally examine the boat. If you find problems you can negotiate to have it fixed.
I've always thought that one can cruise on just about any boat out there--being careful to choose the weather and local conditions best suited to the vessel. So it really is a matter of individual taste/desire and budget, when all is said and done. Our own vessel is a far, far cry from a new charter boat--but suits our purposes quite well: it was originally built for short-handed cruising in high latitudes and being a classic pre-WWII boat, it also carries a style that I greatly value.
I believe many boats with good reputations as "cruising boats" 30 and 40 years old have held their value amazingly well. Depending upon methods of construction and maintenance/use/care given to the boat it can last a very long time.
A boat starts out with whatever capabilities it was designed to have and, well, generally goes downhill from there until a major refit or rebuild is completed. A 30 y.o. boat with a recent rebuild might be an amazingly good deal whereas a 6 y.o. boat heavily used and close to being in need of refit may not be such a great deal. I agree that it's always nice to get new electronics and not to end up paying for something that you don't value--like someone's old electroics.
Another way of looking at things--you can't turn a Jeanneau into a Hallberg Rassy. What do I mean? I have a dear friend who was more-or-less afraid of sailing around in her (new) husband's 30 year old Halberg Rassey. He'd had the boat for years before they married but she was one of those people who believed new is always better than old. She just wasn't comfortable cruising in a boat that wasn't "new". They couldn't afford a new HR (looking at over $1M for a replacement of their 30 y.o. boat) so they bought a new Jeanneau Sun ODdessey for a bit under $300K in 2005/6. She was happy with the new boat. Now, she just sold it in 2012. Why? Ah, because as it turns out she really liked the way the 30 y.o. HR sailed, the quality, and felt the Jeanneau wasn't a comparable vessel even though she says it was a much prettier boat because it was new and the experience of living aboard at anchor/marina was wonderful because it was so much more open/spacious. On the other hand, in a nasty seaway, she felt unsafe in the new boat as she'd been thrown across the cabin a couple times. That wouldn't have happened because of the layout of the older HR they owned. She's now on the lookout for another HR (or similar blue water vessel) to replace the one they sold. My friend's cruising was in Scandinavia and Northern Europe. If she'd been in the Caribbean, perhaps it would have been different--who knows.
So--figuring out what someone wants in terms of a cruising experience--what sort of boat will fit the bill? Then, after figuring that one out, deciding if a used charter vessel will work makes sense. Else, it seems to me to be cart-before-the-horse.
This does all lead me back to the beginning statement of you can cruise on just about anything
Just figure out what you want and why--then make it happen. Remember, its not all about money/cost but rather about what you want to do with the boat.