1996 Monte Carlo LS starting problem

I have a 96 monte ls with a wierd starting problem. It starts better when its 40 below then it does when its 80 in the summer time. It will eventually start by itself but I have to pump the gas in order for it to start within a reasonable time. I heard that it could either be the fuel pressure regulator or the fuel pump. Has anyone else had similar problems? I figure the whole starting better when cold should be pretty problem specific. The idle also runs rather rough and when slowly accelerating from 45 to 65 the motor will stutter, This could be a tranny problem, but I'm not sure. A new tranny is being installed as we speak so I'll find out about that problem when I get it back.

We'll start from cheapest/easiest to hardest here...


-Fuel Filter (possibly clogged? when was it last replaced?)

-Fuel Pressure Regulator (can go bad if your fuel filter is plugged... also can lead to injectors going bad)

-Fuel Pump (when you go to turn your key to the accersory 1 click forward, but don't start the engine, have somone open your gas door and put their ear next to the gas cap, and see if they can hear the pump go BUZZZZZZZ)

A cousin of mine is a Chevy mechanic and he had me replace the fuel filter first since it was the cheapest, no junk came out of it but the fuel that poured out was dirty. I also cycled the key to make sure the fuel pump had ran fuel throught the lines, I could hear the pump kick on when the key was on but it still starts hard. I also pulled the vacum hose off of the fuel pressure regulator and when I put my finger on it to see if there was any fuel it was damp with fuel but it was'nt dripping wet.

any fuel coming out period is sign to replace regulator. would def do that too!