That's a nice design. I'd be tempted to run it through the splashboard to the cockpit.
Once you've sailed into a calm area, you might try using the length of vertical halyard (parallel to the mast) as you might the bow-string in archery. (Tug on the halyard while taking up the slack at the cleat—or in your case, the cam cleat).
A gooseneck that has "worn flat" on the inner surface (as mine has done) has a tendency to hang up while raising the sail. I'm looking for a fix other than the plastic cable ties that sorta help.
P. S.: I've found that a suggestion found at this site (to carry the paddle under the tensioned halyard) works great to interrupt (and slow) those occasional wakes that crash over the deck.
this is all pretty superfluous. I was in pretty high winds (15mph gusting at 20) and I had to stop to do an emergency fix on my tiller/rudder (a bolt came off, should prolly check that before launching). I let the sail down so I could fix it without capsizing, then raised it again with the standard set up on the lake. lol, if you just wanna sit in the cockpit get a speed boat .
Just now seeing this old thread. I've used the pulley system and cap/eyelet system with halyard (for raising the sail). The pulley system is really, really much easier with the type of rope I'm using for the halyard. I'm wondeing now why some people report problems (although minor) raising sail with cap/eyelet and some don't. Leads me to think, maybe, it's the type of rope being used. I've actually been thinking of spraying top cap/eyelet with Pam (yes, cooking grease) before I hoist !! Probably would make it easier but wondeing over long term if it will somehow degrade plastic cap or the rope (or maybe make the mast cap last longer??). Or maybe I should get a different type of rope for the halyard. Right now I'm using non-nylon, very simple, low-tech type of rope.
Get some spectra 12-strand line for your halyard and it will slip through the top cap with no issues. You can go as small as you want (7/64" or 1/8"), but bigger (3/16") is easier on the hands. I'd also recommend a horn cleat on the mast, cheap and can be screwed to the mast. Raise the sail as high as you can easily, make a 3:1 purchase and then use that to tighten the halyard and finish with a cleat hitch to the mast cleat. Then use the tail to tie a cunningham using the deck fairlead around the gooseneck, which keeps the sail attached to the boat during a capsize at a minimum. It can also be tightened to hold the boom down in heavier conditions. I personally tie a second 3:1 in the cunningham so I can crank the boom down if I need too.
Get a little can of McLube for lubricating the top cap. It's a silicone spray lubricant which will not harm lines or attract gunk. It's great for the blocks and the end caps if you have an adjustable outhaul.
Sorry to confuse anyone. I type cunningham, but I was referring to the "vang", which you tie with the tail of the halyard to hold the boom down. The cunningham is rigged along the luff, leading edge along the top (gaff) boom, of the sail. It requires a 2nd grommet and a cleat on the boom.
I still have a supply of plastic end caps with a nice brass Wilcox & Crittenden block on the side. $10 for the cap and block and
$5.80 for a USPS Flat Rate shipping box. E-mail me at: firstname.lastname@example.org if you are interested.