A quick primer on lead bullets:
Three things effect potential leading in barrels.
- Bullet Diameter
- Bullet Hardness
- Lubricant
With cast bullets, you want to size a bullet so that it is one or two thousandths larger than the bore diameter. To determine the bore diameter you can force a cast bullet through your barrel, and measure it. In revolvers, you have to check each cylinder throat as well.
Bullet hardness is more alchemy than science. Two hard and the bullet won't expand to seal the bore, letting hot plasma slip by. This will cause leading. Too soft, and the gasses will cause the tail end of the bullet to solder the inside of the barrel. The higher the pressure, (not speed related necessarily), the harder the bullet you want.
Lubricants can help prevent leading even if the above two things are not exactly right. Softer lubricants work better than hard lubricants. Commercially cast bullets typically use harder lubricants so they will survive shipping. For this reason, they carefully size every bullet, and use a harder alloy.
The main reason I typed all of that for you is the picture you posted of your first attempt.
It is my opinion that you have too much crimp on that bullet. If you put too much crimp on a bullet, it can re-size the bullet when fired. This can cause a now too small bullet to lead a bore.
So: Go easy on the crimp. You appear to have plenty of neck tension to hold the bullet anyways.
Try seating a bullet without a crimp. Push it against a solid surface. If it takes a lot of force to get the bullet to move, (yes I know it's subjective), then you probably don't need any crimp.
If the bullet moves relatively easily, add a bit of crimp until it does not. That is all the crimp you need.
In automatics the problem with bullets moving is called 'bullet set back', where the bullet ends up too deep in the case. This reduces usable case volume, and with max loads has the potential to cause a kaboom.
With revolvers, the problem is just the opposite. Recoil from previously fired rounds can cause the bullet to pull out of the case, causing the tip of the bullet to protrude from the cylinder face, and jam the gun. This will cause much cursing, frustration, and flailing of arms, but no kaboom.
I hope this helps a bit.