Questions regarding lines led aft and rudder options?

[Ed]

   Hello all, as you know I bought Urchin, Windrose 18, from Charles Brennan a few months ago.  After countless questions for Charles regarding the boat he suggested we move our conversation to the board for others to chime in on, so here I am.  So far I've had the bottom painted to keep Urchin in a slip since GA DNR keeps Courtesy Docks at least 100' away from the ramp or closes them when they draw the lake down, replaced the 15hp 2 stroke with a Honda 5hp 4 stroke, donated the 15hp to the Sea Scouts for their chase boat, replaced the original motor mount with an aluminum one with 4 or 5 lowering points rather than the drop the old one had that scared the spit out of me every time, put sail slugs on the main instead of fighting the bolt rope, and put a jib downhaul on.
   Now for my questions. Number 1: I'm trying to decide on how to run the Main/Jib halyards aft.  My concern is turning blocks on the mast just above the mast step running to a deck organizer - concerned about the angle causing friction at organizer and trailering OR put even more holes in the deck and mount the turning blocks in the deck?
   Number 2: Lifting that slab of wood called a rudder/tiller with extension in and out of the boat is a game for those younger than me.  I priced out an IdaSailor/Ruddercraft with mast crutch at $1400 and gagged on that, although I've bought two of them on past boats and liked them.  Sailboatowners.com has an HDPE Rudder Blade that requires custom measurements, but it would still have a better foil shape, and I could leave the rudder on with Becky making a matching tiller cover.  Anyone have experience with the wood/aluminum/HDPE combination on a boat in a slip?
   I made a dockside slime remover using a 15" window scraper from Home Despot and 3/4" PVC fittings that I found on the internet.  Basically a 45 degree fitting screwed onto the metal handle with a 1/2" piece of PVC for the extension.  Zip tied a section of pool noodle onto the scraper that ended up rubbing the crud off the bottom and holding the rig against the hull.  I'll still get the bottom cleaned when I don't pull the boat and clean it myself every 5 or 6 months.

   

[Wolverine]

Not sure why you are lifting the tiller/rudder in and out of the boat. I keep my Compac 19s rudder/tiller on. Even while trailering. I just lash the tiller to keep it from swinging. When not in use, she sits at our dock with the rudder raised out of the water.

[Charles Brennan]

Wolverine, Your statement:

When not in use, she sits at our dock with the rudder raised out of the water.

Is not practical for the geometry on the Windrose 18.
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As you can see here, the rudder would still be in the water for a boat that is tied to a slip.

This pic shows the rudder blade up and still completely submerged.
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In the collage below, it's not possible to let the rudder hang down while on a trailer.  You can see the pintles are several inches above the transom, when the rudder is extended.
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Ed, Your questions:

Number 1: I'm trying to decide on how to run the Main/Jib halyards aft. 

Something I looked at (and never got around to!)  was a halyard organizer plate, like this one made by Dwyer.
https://dwyermast.com/medium-halyard-organizer-plate-dh288/
(Measure, before you order!)

It would be trivial to unbolt the 3) ¼-20 bolts holding the mast step down and then use the mast step as a template, to drill holes for the organizer plate.
I never got around to it, since I didn't see how it would gain me very much. 
C'Mon, Man!  The boat is only 18 feet! All those halyards on the mast, are only about 2½ feet from the companionway! 
(Yer starting to remind me of Damien!) 
But that organizer plate would easily deal with a main halyard, two jib halyards and your (new!) jib down haul.

Number 2: Lifting that slab of wood called a rudder/tiller with extension in and out of the boat is a game for those younger than me.

Hmmm . . . .  not sure I disagree.  Did it myself, for over 45 years.
It IS a Big, Honkin', Hunk of Mahogany.
For me, the real trick was Nautical Jiu Jitsu.
A) Removing the rudder: Lift the tiller up and pull, until the pintles clear the gudgeons.
B) While still pulling, lever the extended rudder on the transom and pull it into the cockpit.
C) Grab the rudder stock, (or the up-haul/down-haul line) near the upper pintle, with the left hand.
D) Lower the tiller handle, with the right hand.
E) Grab the rudder up-haul line with the right hand, close to the rudder blade.
F) Guide the tiller through the companionway hatch and step into the cabin, holding the rudder stock (or line)  and rudder blade line. 
G) Thread the tiller into the main cabin, and lower the rudder blade onto the cabin sole.
H) Hook the rudder up-haul/down-haul line on the starboard hammock hook, so that the rudder hangs.

Did it that way for several decades without issue, but I can easily see how that would get really old, really quick, doing that on a slipped sailboat.

I have to believe that HDPE would be even heavier than the Mahogany but would at least, have the virtue of being easy to scrub off and not getting waterlogged, while continually immersed in water. The longest I ever had it in the water continuously, was a week at a time, down in the Keys, or BEER Cruises or FL 120's.  Never noticed any issues, but a week is far different than a year.

Have to take issue with one comment:

but it would still have a better foil shape.

Check the blade again; I think you'll find that is a NACA 0008 foil. (And swing keel is NACA 0015.)  Further, the leading edge is ahead of the pintle pivot point, so that it is a very responsive counter-balanced rudder.

Hope this helps,
Charles Brennan

[Riley Smith]

I have only a glimmer of your problem but it brought me back to those building days ( since CB is building too) and I didn't have the princely sum for turning blocks. That needed to be installed SOON before it was a REALLY big deal, whose backing plates needed installing while the deck wasn't ON the boat. So I used a heavy duty strap secured with two serious screws for each block. The block was a swivel block shackled to that and had a stainless spring to keep it above deck and a custom stainless washer to hold the spring. On my boat the forces are generated upward on the deck and the whole design holds hands to provide strength. Once at Sand Island one of the cleats FOR the blocks got loose and messed things up, but it has been good enough that I haven't messed with it since. I have often wanted to spring for some really good and easy-to-use clutches but can't swallow the boat buck it would take, so I just use the cleats alone. It's a little different with a gaff rig as you're dealing with TWO halyards in concert, a small amount of slack can make a really big difference in the shape of the sail. I sure love it when I have some crew and I can get the sail pretty, but it's pretty hard single-handed.