Yes. I have.
Since I was fitting a rig to a pulling boat, I reasoned that the keel was too narrow to take a daggerboard case, and fitted a leeboard.
After a couple of weeks, I fitted a daggerboard case through one of the garboards.
The daggerboard case does not take up much room in the boat, and unlike the leeboard set up, you can get to windward reliably with it. You need a cap to the top when towing the dinghy or she will flood through it.
And the answer to the "rigging" question is a standing lugsail, with a simple (rope grommet!) traveller on the mast for yard and boom or they go haywire when you drop the sail.
A very simple rope horse across the transom is handy, too. No need for a purchase on the sheet, but you need about 3:1 on the yard downhaul.
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