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Like this.  Note the midshipmen's hitch is with a doubled up line, each turn is snaped into place below the last turn and pulled tight.  Also the last, locking turn has come undone, I think it's good till the cover comes off in the spring.  Not my best.
Jim

The drains in the cockpit are in the far aft corners in the gap between the aft lockers and the side benches. I know LA Lady isn't the only MkII to have them!

That's the way Shamrock is also.  Because the cockpit floor is angled up at the aft corners they see very little water.   The boat needs to be healed over with the rail near the water for water to collect in that area instead of running out the aft.  I've checked the drain lines, the drains go to a T then a single drain line to the stern drain.  Because they aren't below the water line I don't think they are anything but reinforced plastic, 1/2 inch (13mm) I think but could be wrong.  Can probably be checked with mirror or cell phone if you can point it good enough.
Because the drains are high to the main cockpit floor (at least on Shamrock) I don't think much if any water would be getting it to the bilge from there.  I would suspect other areas.  Aft locker lids?  Emergency rudder hatch?  Both have been sources of leaks on Shamrock.
Are you sure the water in the bilge is coming from aft?  My first season with Shamrock was getting water down inside the compression post then to the bilge from the mast.  Cause was drain hole at mast base was plugged with dirt and debris.
Jim

Mine has scupper hoses! This oddity has been discussed on other forums.

Keelsom,
I'm curious.  Where are the scuppers? 
Jim

Dave,
Thank you for the excellent write-up. 
Transmission failure is a worry.  From what I understand there's little or no signs of upcoming failure and no practical way to check the condition of the transmission. 
Jim

It seems like it should work, but wonder if anyone had experience with this or another way to tie off the halyards with a boat cover. 

I gather the halyards that are forward of the mast, jib, extra jib and spinnaker, attach and tie with a small line to a well used 5/8 dock line, think I use 2 attached together with a zeplin knot then send them to the mast top.  I then wrap the dock line around the forestay, think candy cane or barbershop pole, then thru the jib tack shackle, to keep the foil from spinning, back to a forward cleat.  That stops most of the shaking/pumping of the forestay.   I have in-mast furling, I made up some spacers and line to keep the foil quiet and not banging so the main halyard is also at the mast head.  That way the only sections of the halyards exposed to weather are a couple of inches at the shackle end and what ever is from the mast exit slots to the cover.
I quit using shroud cleats.  I use for my flag halyards what the tall ship people call a midshipman's hitch much like a rolling or taunt line hitch.  I do an extra turn around the shroud 3 total plus the lock turn.  It's the kind of hitch that needs to be formed correctly to work.  I find that I seldom have the flag halyards come loose and nothing for the genoa sheets to catch on.
Jim

Welcome Raymond,
I sail the Great Lakes mostly single handed some of my cruises have been over 1000 nm.  I have a wheel pilot ev-100 that I'm happy with although I believe the wheel drive is not quite robust enough, use it 90+% of the time, but I've rejected a below deck drive.  I intend to carry a spare wheel drive on my next cruise.  I have a stand-alone B&G chart plotter bought as a factory rebuild.  Use my cell phone navtronics apt for back-up but find it hard to see in sunlight.    For me I see no reason to have it all tied together.
I belong to Great Lakes Cruising Club.  Thier harbor reports are a great way to plan a cruise.  Tonight Nov 16th is a webinar you may be interested in presented by their school I think there's a small charge for nonmembers.
https://www.glccschool.com/product/introduction-cruising-great-lakes
Also in case you don't know there is an excellent organization of Great Lakes Solo Racers.  I was thinking of taking up the challenge, but started having health issues and the multi-night sailing didn't sound like a good idea.  I did get many excellent tips from them for safely single-handing.
https://www.solosailors.org/
I would suggest you add boat information to your signature.  Helps getting the best answers to your questions.  Just see what others have done.
Jim

Guys : there is a P. Glycol that goes down to -50 degrees (not pink - kind of a dark green) - That's what I use for the engine!!

Around here it's -100 and using it in mechanical systems, engine, air-conditioner etc is usual practice.   What I was told many years ago by someone I considered knowledgeable is that it's more corrosion resistant and kinder to the rubber parts than the pink.  This may or may not be true, all I can say is that it works for me.  FWIW I leave the impeller in and use it several seasons, when replaced it looks like it is good for several more and I use the boat a lot.
Factoid, read the label on the antifreeze.  -50 or -100 is when it will burst a 1/2 inch copper pipe.  I believe our plumbing is not as robust.
Jim

I started looking for play. It is tight at the cutlass bearing/strut but the play where it goes into the hull is greater than another C34 and C30 in my yard. I seem to have a good tight bolt up at the transmission flange. So my question is: Does the stuffing box/shaft log give the shaft bearing support?

Hi Paul,
The stuffing box/shaft log only gives what support there is with the shaft log hose, not much support there. You said the bolts at the transmission flange were tight.  Did you check the shaft to coupling?  Did you try, or have someone rotate the prop and shaft while you were inside and able to see or hear the twang?
That's just my thoughts.  Have no experience with any sound like that.
Jim

Raymond,
Most of the winterizing has already been discussed.  I would mention, before pouring in the antifreeze bypass the water heater and drain it as much as possible.  My winterization is use the -100 in the mechanical systems, engine raw water and air conditioning -50, the pink stuff, in potable water and head.  Drain transmission and overfill with a fresh quart of ATF, in the spring drain down to correct level.  Don't forget to check that the engine antifreeze is the correct level and right strength.
I'm with Ken, don't see any advantage to using synthetic oil in our Kobata engines.  They were designed to use petroleum oil.  But then if the engine has been run with synthetic I might keep using it.
Jim 

The way I understand it VC-17 is available now in the original color, it's at our local dealer.  I contacted Interlux by the website about a month ago and was told VC-17 red, what I've been using, would be available in this spring.  Hope that's correct information.
Please let me know if you've heard different.
Jim

then took of the topping lift as it was not needed!!

I have a ridged vang but use the topping lift to run fancy dress up the mast.  The main halyard is busy with the inmast furling.
Jim

Hi Andy,
Your motor is different from mine, though they are very similar.  That explains things.  Sorry for any bad information from me.  Now that that you have confirmed the dipstick is correct run it with the oil between the marks, I prefer closer to the top mark.  Sounds like the original operators was missing when you bought the boat, would be a good thing to have.
Jim

Where is the bottom of your dipstick holder?  Mine is just aft of the oil filter.

Are sure it's not aft of the fuel filter?
The dipstick on Shamrock is starboard aft, sort of underneath and aft of the air filter.  Inserts right into the block.  When checking oil I insert it all the way down, not to the bottom of the rubber seal.  Oil drain hose goes to back side of engine.  I don't think it leaves much old oil in at oil change if any. 
Checking oil/fluids is no longer a standard thing.  ie Engine dipstick goes in all the way to check,  transmission goes to where the threads start, not screwed in.   
Jim

I'd seen a post recently about hump hoses being better so I researched them. In my ignorance I was looking for a long one! Your set up looks quite good.

I agree.  Andy, Please post the part numbers you used and the supplier, especially the connection, fiberglass?, tube.  Maybe in a separate thread is the right place.

IMHO.  I think you are doing the right thing asking here.  But, if it were me, I would talk to Westerbeak and Kabota before making any changes to oil level.  Maybe someone will answer with a good contact number.

Hope you solve the mystery.
Jim 

Was at Shamrock this morning and took a couple of pictures.  Note my dipstick is not the same number as yours.  I took a picture of the oil pan with a tape measure so you can compare.  Sorry it's upside down.
Jim