Maybe I am mistaken but your original post sounded like you were looking for opinions on your purchase rather than an unqualified congratulations on your purchase. I am really baffeled by the vociferous nature of your replies. Not having seen the boat I was careful to preceed my comments with the qualiication with this statement:
"As a very broad generality, unless very well maintained and updated by a previous owner, you might expect to need to address some combination of the following items:"
Given this qualifier and the qualifiers at the end of my post, I would say that all of the items on my list are valid, even if they each item does not apply specifically to the boat in question. In other words I did not say that the list of conditions potentially present on a 20 year old boat definitely existed on your specific boat.
My comments were not intended to accuse you of being undiscerning as much as it was talking about some of the things that would normally be considered in evaluating the purchase price of a boat of that age and linage. Your comments that you had evaluated the condition of the new mainsail and the electronics were entirely consistent with my comments rather than at odds with them, so I am baffled by your tone which seemed to reflect hurt feelings thatI might suggest that these items should be considered.
That said I am specifically concerned with your comments:
"I have eyes and I am able to discern things like worn out decks, rotten bulkheads, failed tabbings, worn out rigging."
"As for mast step etc, what do you think a surveyor is for?"
With regards to the items on the first list of items, deck problems are not easily detected, even by a knowledgable surveyor. Teak decks as installed on most Taiwanese boats are fastened with thousands of fastenings that penetrate the plywood decks below. The domestic plywoods used in most Asian built boats was a fairly rot and delamination prone material. Freeze/thaw in cold-freshwater climates and UV degradation in tropical areas are hard on the sealants used to protect the deck eventually allowingw water to reach these fastenings. Because teak decks often fail from below, having ''eyes'' tells you little about the remaining lifespan of the deck. The typical method of evaluating the condition of a teak deck is by sounding them out like you would a fiberglass deck only with less reliable results. In other words even if the decks look good and sound out reasonably well the normal lifespan before a major rebuild is something on the order of 25 or so year.
The way most high quality boats are built today, the areas where bulkheads usually begin to rot, and tabbing usually begins to fail, is concealed by finished materials such as cabinetry, decks and trim. Since few surveyors will do destructive testing, and so are unwilling to disassemble a boat enough to see these areas even with good eyes these items are often hard if not impossible to detect.
Standing rigging at or near the ends of its useful (and I emphasize useful) lifespan is not something that can necessarily be visually inspected. Certainly the rigging can be examined for failed terminals and for broken strands, which are the more obvious teletale signs of the end of the lifespan for standing rigging. But standing rigging often fails from fatigue. While anecdotally individual examples of standing rigging may have reportedly survived in use for 30-40 years, if you are going to count on the reliability of your standing rigging through a wide range the wind conditions, then the generally accepted recommendation is to replace standing rigging after 20 or less years of use, no matter how good the rigging looks. This is especially true of the domestically grown varieties of stainless steel rigging typically used on Asian boats.
Mast steps on many Asian boats contain portions of the support system that consist of glassed in wooden components. Over time these elements will often deteriorate. In some cases the failure mode is a slow crushing, which a good surveryor should be able to detect. But in other cases, such as a Tayana that an owner asked me about a few years back, the owner reported that the ''rig suddenly went slack'' and when investigated the glass covering on the mast step support had given way and the wooden block below that covering was found to be completely rotted out.
You did not talk about the condition of the potentially 20 year old Yanmar and the level of dilligence in its maintenance and use.
My overall point here and in my original post is that it is not relevant whether a bad mast step or any other specific problem with any of these so-called "useful lifespan" items is detected by the surveyor. These items all have a fixed life before attention is necessary. Even if these items appear perfect, after twenty years of normal use, they are suspect and as such they affect the fair market value of the boat. Not having seen the boat, or having heard about its history, use and sailing venue, it is hard to say how by how much.
In any event, my post was not intended to impune your discernment, or the quality of your surveyor. Your original post sounded like you had a question about how good a deal you had gotten on the Nassau and my post was solely intended to provide some information that might assist in allowing you to answer that question for yourself. I appologize if my reply was taken as a personal attack. It was not meant in that manner.