Questions about my Triton rig

[Brion Toss]

Hello,
Where to start? How about with that drifter. This Triton is a fractional rig with jumpers, but that doesn't preclude a drifter or spinnaker. In fact there is a halyard bail clearly visible in the pictures you sent. Perhaps I am missing something, but perhaps your rigger is not familiar with fractional rigs of this type.
Then there's that mast sleeve. It might be covering a repair, but if it is, it appears to be well-suited to the job: generously thick, good fastening pattern; nice stress relief in the shape. It might even be original construction for a two-piece mast. Certainly no indication from here that it would cause a problem.
It is possible -- even likely -- that a boat of this vintage needs attention paid to its rig, but I would get detailed confirmation of the state of things before condemning what is there now.
As for the storm stays'l, are you sure you need one? The forestays'l is already relatively small, and a well-cut roller-furling sail, paired with a good furler, would allow you to reef right down.
Fair leads,
Brion Toss