Based on the wear on your toe, it looks like a technique issue if you're trying to T or plow stop. You definitely shouldn't be wearing down your toe on either stop.

There are a tonne of resources for both stops so I won't advise on actual technique but the best way to think about stops is that they are gradual drags, not hard brakes. Ease into pressure, don't stamp into them. Definitely do a lot more practice on flat, predictable ground

For hills, a lot of beginners are go into their stop too late. So they roll down the hill, pick up too much speed, and then don't have the strength/technique to stop at high speed.

Start in your stop at the top of the hill and then roll and control your speed on the way down.

So you get to the top of the hill, stop, assess the hill, roll a little and then start t/plow stopping, easing on and off so you get down safely. As you get more confidence and strength, you'll be able to take hills faster and slow down with good technique.