sheet leads and hardware layout advice needed

Your right, for what amounts to slow turning blocks your best effort is good enough. What is most important is not to have the hole at a angle or the sheeve will wobble and bind on the cheeks which is why I suggested the drill press. Of course you need to saw the stock square to do this. I've made quite a few blocks as described with no problems at all.

oops, just saw you found a tutorial...

 

Yeah, I had forgotten the part about the hole saw pilot bit. You would still have the same problem though if the pilot hole was not the exact dimension you needed, and you had to freehand a larger hole for an insert or larger pin dia.
I think I am going to give it a try. All I have to do is find the right cutting tool for the groove. Do yours have bushing inserts or bearings?

 

Thanks Bruce. I just noticed in this picture there is a clear view of the traveler car and the two blocks mounted on it. You can't see the clew, but I am pretty sure there is a single block mounted there, so if I understand this setup correctly, there is one continuous line for a sheet- that passes through a block on the car to a block on the clew, and back to a block on the car, and on to the other side? Then the car has stops on the track to limit the degree of travel, depending on the point of sail (but it probably just stays put most of the time?) And then instead of adjusting one jib sheet, like on a "normal" setup, where the weather sheet would be slack, and the other taught, BOTH sheets would have to be tensioned the same way, and the force upon the sail would push the car to one side or the other?

This is probably all painfully elementary stuff to most here, but I am still baffled, pretty much.

 

Most of what I've made have plain bearings/bushings. I don't use a hole saw but buy round stock and turn it down to the required diameter. I've found a small wood lathe gouge works fine for the "groove". I'm used to working freehand though, if you don't know how to use a wood lathe some practice is in order. Really there are a lot of ways to make the wheel, figure out what you have for tools and go from there.