Engine/Transmission (1998.5 - 2002) Cranks longer when on hill

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My friend has a 24 valve that he just bought and it cranked a while before it started. We installed a air dog system thinking the lift pump was weak, but it still does it. Then we realized that when parked down hill it pops right off and when parked up hill or flat it cranks a while, even thought you can hear fuel circulating from the air dog back to tank. Any suggestions??
 
When my 96' did this it was dry rot fuel lines. I replaced all soft lines. I think the 24v soft lines are slightly different than the 12v. On my truck the major problem was the fuel preheater to lift pump. When I cut it open I could see daylight through the sidewalls. It did not leak fuel, only sucked air.
 
I'm experincing the same problem. In the cold the (below 40) it won't even start with 2 grid heat cycles. I can roll out in the street and everything is fine. Park nose down and everything is fine.
 
Definitely air getting into the system. I had a 99 that did the same thing. The leak was in the return line T connection on the the drivers side, rear of the engine. If parked nose up it would crank and crank, nose down it would light right up. Definitely check for any wet spots on the line, or start replacing the soft return lines.
 
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