Good thinking

AND I do appreciate your thoughtfullness. Warm regards, Roger
Of courseSure it could be done. But the question is, what would you have after you spent all that time, effort and $$$$. What I see as the obstacles on your mission are:
A boat with the convenience of a powerboat, with a sailing option, that an aging guy could handle easier than scrambling around solo tending to all sailing chores. (Even from the cock-pit.) I think???
1. Installing a mast
Adding deck support/compression post.
Bulkheads for chainplates.
With a Non-Such mast, no stays, some of that is eliminated. Reinforcing is needed.
2. Directional control
Rudder. Depending on your boat. Where would you put it? Single rudder if it won't interfere with your screw(s). Dual rudder like a MacGregor.
Keel (if you choose that route) would have to reinforce the hull. So you'd have to tear up the cabin sole to do that. But a lead or iron keel would help keep the boat upright as well as side windage.
Leeboards, easier than a keelbut would still require hull reinforcement
MacGregor-like-double sounds practical. . .
3. Positive stability
Installing a weighted keel.
I think the weighted keel would be my choice, even with the work involved. Although lee boards do have some advantages.
Making it a multi hull. This would actually help with steerage as you could put your rudders and daggerboards on the outriggers.
Could do, but the extra width might be a problem??
All in all I think it is feasible. But just in a "I told you I could do it" or "Look what I did" sorta way.
You're probably right. . .But innovations do lead to convention in the odd case.
BTW, my Grampian 23 is named, "Y-not?" My sorta personal philosophy. . .
Disclaimer: All the above is IMHO of course.![]()
AND I do appreciate your thoughtfullness. Warm regards, Roger