Dean,
Your quest for this data is like a dog chasing it's tail. Kind of circular and really not going to give you a "realistic" number as there are soooooo many other items that can cost huge $$.
You are looking at some old boats with some older systems they will ALL cost a significant sum to own, maintain and make safe and fit if you're not focusing on only boats that have already had all this work done..
You don't even want to guess what a teak deck will cost to fix, or wet decks.... A ketch or yawl rig will always cost more to maintain than a sloop or cutter. Winches last nearly indefinitely and all but the oddest winches can be disassembled and greased in about 40 minutes per. If you can live without self tailing winches than your fine but a boat I'd be focusing on would have had the PO already upgrade them to self tailers.
The best advice I can give is to ALWAYS buy the best condition boat you can. Only focus on vessels with MASSIVE amounts of upgrading done by a previous owner. Do not reward the a lazy seller by buying his or her unmaintained junk. The "deal" is most often not a "deal" at all it can very often be a never ending $$$ pit. Buying a boat that is in tip top Bristol condition, by FAR, will cost you less than thinking you can beat the odds and "fix it up" for less.
Tell your broker you will only look at boats in the top 2%, condition & maintenance wise. Put this criteria on paper and define what this means. If he sends you on goose chases to boats with tattered sails, dirty bilges, olde rigging, tired engines, chalky top sides, moldy interiors etc. etc. FIND A NEW BROKER! On boats of this vintage avoid teak decks at all costs, if you value your money...
Even when buying a "two percenter" I still set aside 20-30% of purchase price for first year upgrades.
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Originally Posted by Dean101
At this point I'm mainly interested in comparing material costs such as standing and running rigging, paint, ground tackle, and other hardware such as winches, blocks, and even sails specifics. I really don't know how to go about finding out wire/line diameter and length, square footages, winch size, etc. to use in figuring replacement costs.
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On boats of this age these items are a small portion of the expenses necessary to get them in safe shape if you're not being a discriminating buyer.. Electrical systems on these boats should also be considered as should chain plates, engine, decks etc. etc.. A boat of this vintage with original wiring is a SCARY thought.. 55% of boat fires are electrical in nature and the marine environment is not kind to electrical systems....
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Originally Posted by Dean101
Since even boats of similar size have widely varying degrees of maintenance associated with them, my intent is to have a sheet of specifics for each boat as I fine tune my list of prospective buys. Any help in this regard would be greatly appreciated. 
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They don't have to have varying degrees if you limit your search to boats that have ALREADY had this work done. These two percenters are out there but you need to be ready to pounce and not hesitate when they come up, as they go fast, even in a bad economy. Discriminating buyers, who know what they want, are out there waiting for them. These boats ALWAYS cost you less even though the purchase price may be 20% higher than a sister ship that is in the 50th percentile of condition.
Be patient, define your standards, and find a broker who can locate what you want a not send you on "junk" viewings..
This is just an example of defining what you want for a broker..
Dear Broker,
Vessel Type
We are looking for a full keel CCA type cruiser between 36 & 42 feet with a budget of XXX. I feel this budget is reasonable but would like to sit with you and examine some SoldBoats.com data to be sure we are in-line with our expectations.
The vessel we are looking for should be well built and will not include XXXX, XXXXXXX, XXXXXXX and XXXXXX brands. The prospective vessel needs to be in the top 2-3% of condition for boats of her vintage. The proverbial "needle in the haystack" that you have ten customers waiting for. We would prefer a cutter but if the right ketch or yawl came along we would certainly consider it.
Rigging, Canvas, Sails
Systems such as standing rigging, sails, running rigging & canvas shall all be no more than 5 years old with documented receipts.
Engine & Mechanical
The engine will be in top condition preferably re-built, with adequate documentation, or repowered. The engine room will be clean and the engine will exhibit no oil leaking or excessive oil consumption. Fuel tanks will be clean and have records of fuel polishing, new tanks or tank cleanings. The tanks will preferably have inspection ports.
The electrical system shall be up to date and be 100% safe and meet as many of today's current safety standards as possible for a boat of this vintage. The vessel with preferably have been re-wired or partially rewired within the last 10 years. The LPG and plumbing systems will also be up to date and meet current safety standards. The vessel will preferably include an upgraded alternator and charging systems and the battery banks within three years old. We would prefer the boat to have solar, wind or both but this is not a deal breaker just a "nice to have".
Refrigeration system is a must and will be in 100% working order with records to document maintenance. An engine driven system is preferred but not a deal breaker.
Seacocks and below water fittings will be well maintained and preferably recent. Seacocks should be open ocean ready and will ideally be proper flanged/bolted seacocks. Below waterline hoses will be within 5-7 years. Backing plates for seacoks will not be "soggy".
Electronics
The electronics will ideally be less than 5 years old and include wind, depth, speed, VHF, EPIRB, autopilot, GPS/Plotter and Radar. Radar overlay preferred as are helm mounted electronics but not a deal breaker if not.
The vessel will come with a full compliment of equipment, engine and systems spares, multiple ground tackle systems etc. etc..
Hull/Deck & Under Body
The hull deck and under body will be in top condition. If Awlgripped or painted the hull will be shiny and not exhibit scratching, gouges or other areas of peeling or blistering. If the vessel is painted the paint will be less than 6 years old. If gelcoat the gelcoat shall be in top condition shiny and presentable beyond 97% of her peers. The underbody will have documentation of being paint peeled, examined for osmisis & ultimately will have been barrier coated. Bottom paint will be smooth and exhibit no peeling or delamination or flaking from the substrate. The rudder will be dry and safe for passage making. We will not look at boats with a cored hull below the waterline. We will not look at or consider boats with teak decks or wet decks. Exterior teak will be maintained to top standards and be in very good shape.
The boat will have documentation of deck hardware rebedding and the deck will be dry. It will not have deck leaks from deck hardware.
Running gear will be in perfect running condition with a tight cutlass bearing, no vibration & good prop. The prop & under body metals shall not exhibit any signs of dezincification of demetalization from corrosion.
Interior
The interior will be clean and not stink like a musty boat. Compartments, bilges and storage lockers will be clean and free of mold and mildew. Cushions will be recent and preferably within 5-7 years. Fabric will not be "outlandish" and will be of traditional boat colors. If the interior is varnished the varnish will be in good condition. If the interior is rubbed oil the teak or mahogany will not exhibit staining or mold issues. The cabin sole will preferably be varnish or polyurethane. The port lights & hatches will be free of leaks and the glass or acrylic will be free of fogging or crazing. The cabin will not have any active deck leaks.
We know this is a tough find but we are patient buyers for the right boat. If you know of this boat, and it is not for sale, I would fully expect you to investigate it anyway. Many boats are "for sale" even when not technically listed.
If you can find us a boat that fits our criteria you will be rewarded with an easy no-financing required transaction, a speedy survey and a cash bonus/tip, beyond your commission, upon closing. We are picky & discriminating buyers but also very reasonable and we look forward to working with you.
Please, above all else, don't waste our time sending us on wild goose chases to view sloppy ill maintained vessels. If you don't know the boat, or have not personally been on it, please be honest with us up front. We love honesty beyond anything else!
Blah, blah blah...
Setting standards of communication up front goes a long way to a good buying experience. You need to decide what your standards will be as this is just a short guide similar to what I communicate when buying......