Nothing weird about it. The halyard goes over the little sheave at the top, comes down inside the sail track, and out around the little sheave at the bottom. Since yours is an '88, it probably has the separate ring and shackle. I prefer these over the welded up ones. First make sure the sail feeder is a tight fit when the bolt rope is started in it. If there is extra space between the sail and the opening in the feeder the sail will get jambed when you get it up enough so the luff curve makes the boltrope want to come towards the back. If the sail is not a pretty tight fit in the feeder to start with, and they never came like this, take a pair of pliers and gently squeeze the jaws together. If you squeeze it too closed, don't use a screwdriver to pry it back apart. I used to use a maple wedge. You don't want to leave a meathook inside the jaws or it will shred the cloth around the boltrope. Just be careful squeezing and it's not too hard. With a properly tuned sail feeder, the sail will go right up all the way. I used to do this with every boat I assembled that left my shop. None of my customers had trouble getting their main up or down.
If you have the separate ring and shackle, and probably also a flapper on the hook at the top (also my preferred method), let the halyard hang loose above the grommet in the head of the sail until any twists come out of the line. Make sure the halyard is tied to the ring with a simple overhand stopper knot holding a single half hitch. The stopper knot needs to go on the side of the mast opposite the hook. Once it's hanging freely without spinning, put three or four twists in it so it will automatically turn the ring back towards the side of the mast that the hook is on and then attach the shackle to the sail-that way you don't have to screw around playing with the mast rotation to get the sail to hook.
Now with a properly tuned sail feeder and the prepared halyard, all you have to do is pull the sail up. I keep a tug cleat on the end of the halyard in case I want to raise and lower the sail on the water to tune batten tension.
If the boat is sitting on the beach with enough room behind it, the boat pointed into the wind, I just take the tug cleat and walk backwards to pull the sail up. As you get close to the hook on the top, look up and stop pulling right after it lifts the flapper and it will drop right in the hook. I use some small, non-stretch line to give good control of the last inch or so.
If you have the welded ring and hook with no flapper, then you will have to screw around with the mast rotation to get it to hook and you won't be able to raise the sail by just walking out behind the boat.