Carpediem, you kept me up last night

I gave this some thought and realized we may be overlooking something, the original thought/assumption (mine anyway) you proposed was about installing what I thought would be a typical inline check valve somewhere along the length of the discharge line. While this is not a good idea for a few reasons we already mentioned, I should however also point out that there are pumps equipped with built in check valves. These would be an option if part of your mission is to prevent discharge water in the line from dumping back in to the bilge once the pump shuts off. These valves are usually located right at the discharge port which solves the air lock problem. These won't however remove
all the water in the bilge for reasons mentioned above. One must also keep in mind that other caveats mentioned above. Here is an excerpt from Johnson Pump about that....
"....NOTE: The check valve supplied with your pump is used to prevent the backflow of water. The utilization of the check valve requires you to be
mindful of its functionality. The check valve material is made of Nitrile material to be used for water applications only. Also, the check valve will reduce the flow of the pump. If flow is critical to the application of the pump, it is recommended that the check valve not be used.
Also, when winterizing your boat, remove the check valve to avoid ice formation and/or degradation of the check valve"
As mentioned before, this won't affect you in CA but up north these must be winterized if the check valve option is used (it comes with a valve but you don't have to install it). I've had to replace a couple of these on a boat that had them new from factory because the owner didn't realize they had to be winterized. The ports split. Most guys don't bother installing the valves for this reason or remove them a couple of winterizings later because they simply add another step and one more thing to remember.
Here is the type of pump I'm referring to. This is the Johnson Pump version but there are other brands with the same discharge check valve option...
https://www.spxflow.com/johnson-pump-marine/products/heavy-duty-submersible-bilge-pumps/Hope that helps
Chris, apologies for the course change here. Did you consider a path to solving your discharge replacement problem yet ?