The tack plates are not supposed to go inside the track. I can see by the pop rivets that your tack plates have been replaced, at some point. They were probably installed too close to the bolt rope.

Can’t tell for sure from those pics, but it kind of looks like your downhaul line is cleated off. If that’s the case, then the sail certainly won’t be able to be raised high enough to hook the halyard.

Release the downhaul and take the gooseneck (stainless steel slider that the front of the boom connects to) completely out of the track. You can even push the bottom of the sail up the track by hand if necessary (grab the bottom batten and push up). Then pull the halyard the last bit. Some lubrication (silicone spray) in the sail track will also go a long way towards making it easier to hoist your main. Only after the halyard has been hooked install the gooseneck into the lower sail track and tighten the downhaul.

I don’t think the condition of your tack plates has anything to do with the issue you’re experiencing. However, one of them looks like it is completely broken at the hole where the gooseneck attaches, so they should probably be replaced.

sm

i rub vigorously into the bolt rope with a bar of paraffin wax. hardware store purchase and 1 box is lifetime supply, ya those plates look shot. i would redo those rivets at least. drill them out and remove plates to see if holes are diff in the sail. with the plates that bad, it is possible that original holes in sail were torn out? move the plates a bit to get into better material? if so, patches/reinforcements need to be sewn onto sail and repaired properly. just thoughts