>>1772698What kind of pump (or pump head) do you have? I'm assuming you're using a track pump w/ a hose.
For now, try the "one foot" method (literally hold the pump head on w/ your foot while you pump), but it's a bit of a balancing act.
For the future: Lezyne pump heads thread onto the valve core, so the thing won't come off til you let it. You can buy just the head, or head+hose from them, and I've converted several of my friends' cheapo floor pumps this way. (I've heard people say Silca heads work well with smooth presta stems, but I've never used one myself.)
>>1772748I've used the same OnGuard lock since 2013. If they still make the same model, I would buy it again. The paint is gone, but I think it's the smallest they offered, Bulldog was the branding. Inside the loop is 3 5/8" by 6" (fits one bike), weighs a bit under 2lbs. I don't use a wire rope or chain, just lock the rear wheel through the triangle.
Why? Each side of the U has a locking pawl, so you can't get it off by cutting just one leg. The lock is key retaining; if it's in the "open" position, you can't pull your key out (prevents the error of going through the motions, but not actually locking it).
The lock mechanism is slider style (can be picked with normal tools, but... brute force is common, not lockpicking). The point here is that the key goes right in, smooth action, even when the key is old.
I can't count the number of times I've seen my friends messing with their Kryptonite locks, jiggling the key, hoping it will open. (All of the Kryptonite keys I've seen are disc detainer type.)