I recently acquired a used TI and I have a project I want to accomplish. I want to be able to fit a flag halyard to the top of the mast and be able to run a flag up and down without interfering with the rolling of the mast and obviously without weakening or damaging my mast.
I have figured out how to mount the bottom of the halyard. My boat came with an anchor trolly on the port side so I can attach the bottom of the halyard to it forward of the mast so it won't interfere with the sail. Almost like a stay on a normal sailboat.
The bigger problem is the top of the mast, somehow I have to get a block up there that is mounted to a free-swiveling bracket that is attached to the mast. The closest thing I have found is what "stringy" did for a rotating go-pro mount. (see picture near the bottom of the page
https://www.hobie.com/forums/viewtopic.php?f=71&t=58118) He made his from a swivel caster wheel assembly attached to what looks like a PVC topper for the mast. That looks like it should work, my only concern would be if it is somehow damaging the mast to have a topper like that. But before I go that route I wanted to check if anyone else has tried putting a flag halyard on their island or how they would go about it if they were to try. My goal is that in a short while this topic will end with pictures and video of me running a flag up my mast.