Opening Pool and Pump Not Priming

[HemiPool]

Hello all and thank you in advance for any help! I will try and be as informative as I can.

I just bought my house, and the pool and all equipment were already here obviously. I now live in Kentucky, where pools are winterized, as opposed to Texas where we never really had to worry about it. That being said, I have been learning quickly what all has to be done to get the pool operating. I have removed the plugs from the skimmer and the return lines, and replaced plugs in the pump, filter and reconnected the line to the multiport valve. Installed the pressure gauge and tightened the filter belly ring. I filled up the pool to almost the top of skimmer outlet in the pool.

Now for the fun part; I filled up the pump with water, turned the main drain on and the skimmer off, and flipped the switch. Pump kicked on, shot water out of the waste line until the pump was empty, and that was all she wrote. I have been trying to manually prime the pump, and have spent hours on it trying to get it primed.

I have already replaced the o-ring in the pump skimmer, and lubed it up. When I attempt to prime on the skimmer side, I can feel suction for the first maybe 30-45 seconds and then once the pump runs out of water(except the little bit that always is in the bottom of the pump), the suction dies. My assumption is an air leak somewhere, which is why I changed the o-ring.

My pump equipment is up hill from the pool and roughly 30-45 feet from the skimmer and main drain.

My pool is an inground pool, roughly 15'x30', vinyl liner.
Pump is US Motors model number - K63CXERW-4785 I believe. (Label is almost white from age) 1 Horse, 3450 RPM
Filter says Hayward Pro-Grid D.E. Filter, but I could not find a model number anywhere. I thought it was a cartridge filter due to the insides, but I guess it is a D.E. filter.
Also have a Hayward H Series 200 heater, and a Hayward Clorinator(SP?) model number CL 200. I will attach pictures and will take more if needed.

As I said, I am very new to pools, so please explain like I am 5. lol.

Despite looking into how to attach pictures, I cannot find a way to post them on the main post here, but will add all pictures on a quick reply where the Full Editor and Preview Button is located.