I've had similar experiences with boots. I used to have a pair of Hebo trials boots. I kept smashing my toes on the rocks here and after losing a couple of nails, I decided to look for something else.
I bought Gaerne oiled boots. They have a much stiffer toe box than the slipper like Hebos. Even Garne's own cheaper boot doesn't have as stiff of a toe box.
I also second the motion on Sidi Discovery Rain's the new version of the old Discovery. They are flexible enough to make a decent trials boot, especially after they are broken in. A number of riders around here use them as a trials boot only. Plus they are protective enough to wear as a trail riding boot. Not sure if I would want to race in them, boot they work nice. This is the boot I wear when we go to CO trail riding. Good feel, good protection, comfortable to walk in and WATERPROOF. Only downside is, they are expensive.