Does the second pump have a pressure tank to add pressure sealing to the closure of the new pumps check valve ?

No presssure tank for the second pump. Only the first small pump has the precharged tank.

hgiljr, I speculate that when the system is shut down, the pressure tank 'pushes' its priming water past the check valve of the second pump thus creating a smaller volume of water for its own priming at a subsequent start up. When the system is restarted, the new pump, because it is already primed, has a "heads up" (I like the pun) advantage over the other. When the older pump has pulled enough water from the system and primed itself, only then will it begin to function. I do not know if all this is going on and I cannot think of a way to verify it. I suggest that you remove the check valve of the new pump and see if that works. Hopefully this will be easy and enough water will be held in by the older check valve to prime both pumps. This speculating has been easy and interesting; from here on it might be only hard work. I can relate to that and so I wish you success in this effort.

Why would the precharge tank cause this? There are two check valves for each pump. Also if I turn on the new pump and it primes itself and works fine. One I turn it off it loses the prime without me turning on the older pump/precharge tank.

maybe i just dont understand where you placed the new check valve in relation to the well and the new pump but i think its this palcement that is causing you to lose prime. my thoughts are that one GOOD check volve placed between the "T" and the well pipe will end the problem.