Has anyone devised a system to roller reef a stay less main with 18 ft mast around mast or boom sloop triangle sail with a boom and main sheet cat boat .
I believe something like a Hobie tandem island mast and sail does that. This Shell Blue Heron sprit sails do that with their stay less masts.
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Consider looking at the cat-rigged Catalina 12.5 Expo and Catalina 14.5 Expo too, as possible examples.
These both use a rotating stay-less mast and a loose-footed Main on a Hoyt boom.
Appears to me to be a clever system if seeking operational simplicity.
My sea pearl is a good example of what you're asking, I believe... Mast drops into a pvc receptacle, boom attachment is free to rotate as the mast spins (after unclipping the boom vang), easy to reef, just roll it up and allow the foot of the main / mizzen to retract as you do, and then cleat the outhaul.
All good if no battens.