valve stem /tpms

Getting ready to go on an extended road trip. Was looking at the tires and noticed that with the cheep short rubber valve stems the tire place installed that I can neither install a tire pressure monitor system or even get my air chuck on the rear duallies. The shop that does most of my rv repair work said he could pull the tires and replace the stems if I bring him what I want put on there. Problem is, what do I want? Does anyone have a setup that works well, both valve stems and monitor system? I'm looking for something that is easy to air up inside dually as well as solid installation that won't leave me with a flat tire due to system leaks.

Seems that the nuts that hold the hub caps onto the wheel only go on about 1 or 2 threads. during normal work hours, nuts need to be fully engaged with 1 to 2 thread protruding, not just partially retained. is this normal?