So...are you using a pump with a Schrader head and are using a separate adapter to connect to the Presta? If so, first I'd recommend getting a pump meant to pump Presta. And if I read the title right, this is happening for both your hand pump and your floor pump?

Anyone that rides regularly should have a good quality floor pump given that you should inflate your tires before every ride. $25 - $40 will get you a good pump that will last a long time. I like my Park floor pump but if I have to replace it, I'm going to get a pump that has the gauge at the top of the barrel so I can see it more easily.

As far as hand pumps are concerned, they're primarily for tire changes and aren't really good for easily getting to the high pressures of a floor pump. I have a Road Morph and the few times I've used it, have had no problem getting up to 100 lbs, which is plenty to get me home. I also have a combo CO2/hand pump...it takes a lot more effort to get to 90 lbs but I can do it.

Finally, with respects to getting the pump head onto and off of the valve, the method that works best for me is, with the bike on the ground, position the valve so it's at the top of the wheel (pointing down). While pressing down on the top of the wheel with one hand, push the head securely onto the valve (don't forget to open the valve first!) and flick the lock lever to secure. Pump up your tire to the desired pressure. To remove, open the lock lever and grab the pump head with your hand. With the other hand, straddle the wheel with your thumb on one side and your fingers on the other, placing them on the pump head. Use your thumb and finger to apply pressure straight down while gently pulling on the pump head with your other hand. Close the valve.

Also...most tubes have threaded stems...but I ended up with some tubes that have smooth stems...as soon as I release the lock lever, the pump head is basically pushed off of the stem.

Hope this helps.