My happy experience was only on the i-sail, and mine did great upwind but as you turn to broad reach or down wind the sail gets kind of shapeless due to no boom. There are discussions on the kayak sailing topic on how to improvise a boom, and stuff like putting a ratchet on the sheet to relieve hand pressure (not so safe due to need of instant payout in gusts).
You may want to install the oversize rudder to handle larger waves yawing you around. And maybe larger turbo fins. Keep them in the down (daggerboard) position, which means the pedals are up together; you can fashion bungees to assist this. Most youtube videos seem to leave the fins in the most useless horizontal position which they will drift toward if unattended.
You can pedal while sailing which is sacrilegious to me because how can you tell if you have it tuned right? Especially when tacking into the wind; you should never ever need to pedal that turn if you have any finesse at all, yet everyone does it. I do approve of pedaling while sailing close to the wind, like less than 45 degrees. It's like motor sailing where your effort increases windflow symbiotically.
Here is a great sailing tutorial on a 2019 Hobie Mirage Outback:
P.S. on the issue of rolling over. I don't think clunky outrigger floats are needed but to be safe use a lanyard to every moveable object in the boat. Clip in pedal fins, cargo, and put an elastic line to your paddle. In another outback sailing video below, note how he awkwardly weight shifts in his sling seat. Try something like a convex pad, maybe inflatable, that lets you lean and counterweight. I had a whole inflatable seat that let me effortlessly manhandle the weight shift.
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