Ok update for the gentlement who where helping me.
Pulled the pump, checked the line, and even replaced every point of contact, where a possible leak could occur.
Rebuilt the whole well head, as it needed to be done.
We tested the pump using a large Trash can, and got great water flow, we then hooked the 160' line up, and it pumped, but we shut it down as there wasn't enough water in the trash can to fill it all the way.
Dropped the pump back into well, tested again, works fine.
Hooked up to main house, at this point water is still turned off. Breaker tripped once, while testing with a garden hose, however the water is very cold.
Took hose back off, hit the breaker again, and tested at the hose faucet, water cold, no problems.
Came inside, been sitting for about 10 minutes, no water still, however, we can feel air being pushed out of lines.
So at this point, if water doesn't come on, I'm thinking a leak some where else, beyond the pump.
Wife just said, water started in kitchen, just a tiny stream. but then it stopped.
I can't help but wonder if it's not the darn breaker again... although, it is a 110 line, when I tested it the other day, there was no problems, I believe it was hitting between 110 and 120.
Which makes me woonder if it is not the pump.
I know when we tested it, it did have a slight rattle, but the pump worked just fine. The pumps Check valve was fine as well.
I did, try and put a new check valve on, right at the pump, but there was not enough water pressure in the garbage can to open it up. So I took it back off, which I will later put up top of the water line, right before it goes into the tank.
Just gonna sit here for about half an hour and see what happens.