So yesterday, I had to walk home because my front tire was flat. I ride a vintage road bike and my front uses schrader, btw. It turns out, the valve was partially severed from the tube. So I switched it out with my backup, made sure the valve was pointing straight, and everything looked normal. And this morning, the front tire was dead flat again. I didn't have time to check what was wrong with it, but I suspect that the valve got severed again, because I checked for leaks on the tube the night before. When pumped up, the tube is uneven with some places thicker than others, but I didn't think much of it.
Am I putting too much pressure into my tires? I try to get it around 100, which I assume drops to ~90 when I remove the pump attachment. One thing I noticed was that if I pull too hard on the valve when I try to detach the pump, the valve would start sticking out more, with some of the rubber tube dragging out at the base of the valve. This happens almost all the time to me with my bike/pump. At that point, I would just release the air and start pump all over again.
Do I need a new pump? Am I doing something wrong?