Pump Losing Pressure - Need Additional Ideas

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Thank you @Rancho Cost-a-Lotta and @BillyMac96, I ran a temp hard line from the pool to the pump, and what do you know, the pump primed again! I've got water moving again - thank you again for your help! Although the pump does prime, it does not prime perfectly as there is still some air in the basket (pump basket gets 3/4 full with water), and it slowly drops to 1/2 full with water after running for half a day. My hypothesis is that I think I have a weak seal at the drain plug, as I inadvertently bought a non-oem replacement. I have the official Hayward plug arriving today which I will replace. Although I have seen no water dripping from this plug, I guess it can still pull in some air from it.

My next challenge will be to determine where the failure is on the piping from the skimmer to the pump. My first hypothesis at this whole problem was a clogged skimmer line (as I get tons of debris in the pool), but I had two different techs blow the line with compressed air and CO2, and no blockage was found. I guess it may be in the PVC joints/fittings above ground where it attaches to the pump (as I already replaced and lubed the gasket there?
My skimmer basket has two holes, and we think one runs to the floor drain in the pool, but the tech could not blow air through through that line and out the floor drain - so maybe this one could be clogged and causing this whole issue? He also mentioned that this line from floor drain to skimmer basket is sometimes capped (don't know if that is true), which is why I did not pursue cleaning this route initially. Don't know if I should try to snake this myself, or camera it.

Temp solution:
Pool Temp line.jpg
 
It's weird that your pump is not completely priming with a direct line to the pool. I will mention that the fittings on your temp line appear to be DWV fittings, not rated for pressure. The sockets are more shallow than pressure rated fittings and are more susceptible to leaks.

I'm hoping maybe one of the other experts monitoring the thread may have some ideas. I'll also ping @mas985 for advice.
 
I appreciate it. Thanks for the dmv note there, I never knew that. I’ve covered the drain plug in Saran Wrap, and that has not helped. Don’t know if that’s where the air is getting in. I’m getting much better flow into the pump from the line than I was originally, but the basket is back to being at 1/2 full. Almost low enough where I would turn it off again to protect the pump from burning up. When priming, the basket fills to 90% water, then drops to 75% at normal operation ~2100rpm, then down to 50% after a few hours
 
I'm far from an expert, but in my opinion, that kind of rules out a suction line leak. It sounds more like an issue with the impeller or something going on with the filter. Hopefully you'll get some assistance from our qualified experts.
 
That’s a good point. The filter was clean before, but the pool was in rough shape. So running it for 24 hours may have led to the filter already becoming backed up and very dirty (pressure has gone up maybe 25%?). I’ll clean it in the next day or so. It’s got a brand new impeller, but maybe it’s now on the filter side like you’re saying. I really appreciate your help - as you had the great idea of the hard line to help with troubleshooting
 
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