IMHO the Stearman wins handsdown. (Will also win going over on it's back.) There's not a Stearman in existence that hasn't been ground looped. And not very many Stearman pilots that haven't ground looped. But there is a big plus and that is it has lower wings so does't tip nearly as much as a 195 does, and it's wood and fabric, and the gear is super strong, so the damage is generally a lot more minimal, and a lot less costly.
Interesting take on the 180 Cannon. My feeling would be exactly the opposite. I've never felt like the wagon was about to get away from me, and even with 29's I have good forward visibility (6' 5" tall helps) on T/O & L. The Stearman on the other hand, even with the seat all the way up, has zero forward visibility on T/O & L. Of course I got my tailwheel endorsement in a Stearman so scary time was all spent in her. Having said that the Stearman is much easier to handle in a crosswind then a Wagon.
And having said that, a friend that has a P-51 and a 185 told me he felt the 185 was a far more difficult plane to control on T/O & L then his P-51. And he told me that while sitting in the cockpit of the Mustang for 15 minutes letting the adrenalin subside after just scaring the crap out of himself after bouncing a landing and getting one of the mains off the runway into the dirt and riding her like that for 3,000 feet.
So I guess what I'm trying to say is Eduardo, I think we can draw one conclusion from this, instead of a Stearman or a 195, or even a Wagon, it appears the best plane to get your daughter is a P-51! Should be able to marry her off fairly quickly too!
