Actually the mast itself is not the problem as that can be easily strengthened by drilling the bungy that goes up the center out then then jamming a fiberglass pole up the center (an old fishing rod or one of those fiberglass driveway/yard reflectors. Or you can slide an aluminum Home Depot painter extension pole over the stock mast (all really cheap options), or you can get fancy and replace the stock mast with a 7/8 dia fiberglass pultrusion rod (they are also fairly inexpensive).
If the sail is too big the problem comes up that the mast holder socket in the hull is not up to the task from the factory. What I did on one of my kayaks was take a 6x6 piece if cutting board with a hole in the center slid it over the mast receiver inside the hull then gobbed a bunch of silicone on the bottom surface and stuck it to the hull bottom. I then did the same up near the top with a smaller cutting board shaped to fit then trapped into the area below the mast receiver at the top of the hull on the inside of the hull. Nothing on the outside of the hull, and everything is removable if you sell the boat. I like using clear silicone because it is all removable and doesn't come loose if you have enough surface area (a 6x6 plate glued to the hull bottom can withstand about 3000 lbs of lateral force, and flexes with the hull if needed), all simple and easy to do even if you can't reach in there easily.
On both our revo's and oasis we were able to add jibs and spinnakers with no difficulty once we re-enforced the mast receivers. However you pretty much have to run a weighted center board or sidekicks to sail with that much sail area. As long as you have roto furlers on everything you can control how much sail to show and use what is needed at that moment. We put many thousand of miles on all of our kayaks over many years with these setup's, it's not worth doing if your not that much into kayak sailing. We sail mostly around south Florida and the keys all year round (we are pretty much out there every weekend, so it was worth it for us.
In my opinion if someone doesn't want to go all the way to an AI or TI, that revo 16 properly equipped with the dagger board would be a great kayak sailer. I still contend though that if you don't keep that mirage drive in and use it all the time you lose 3/4 of the capability of the Hobie kayak as it was carefully designed around the mirage system. If you only want to pure sail just get yourself a sunfish instead, way less effort to pure sail, I like kayaking way more than sailing you can do so much more with kayaks IMO (unless you really like sailing around little buoys in boats designed in the 60's that your not allowed to modify at all, many people do, it's just not for us). I still have yet to see anyone fishing from a sunfish or laser, or any doing anything besides zig zagging back and forth a few hundred yards from shore with no destination in mind. I have only ever seen a couple at the sand bars and islands we like to hang out at. And I don't think I have ever seen one all loaded down with camping gear. I'm just sayin...
Hope this gives you some ideas,obviously we love kayak sailing, and IMO there is nothing out there that even comes close to Hobies stuff.
Bob
Below are some of our old rigs for your viewing enjoyment:
Our old Oasis:
One of our Revo's:
one of our TI's:
One of our TI's setup for kayak sailing (with a 33 sq ft wing sail, (weighted center board required)):
This is our weighted cantilever keel (can be pulled side to side to balance boat, fits in mirage well):
Here is me sitting on the rail of our TI testing the weighted keel (notice I'm wet, I was unable to stand on the rail (balance challenged LOL)):
Personally we have a blast with all our stuff, and use the heck out of everything.
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