I would not run any kind of rubber hose near the headers. I got new trans lines from Summit Racing for $35, and I'd go to new ones all the way to the radiator. At that point you can cut off the ends and run hoses to a remote cooler.
I don't run mine to the radiator, as I like my trans coolers isolated from the radiator heat. I just have two short 3/8" hoses from the ends of the lines to the trans cooler.
If you get a couple compression fittings you could splice onto your present lines and extend them, but with the fittings and line you might be in almost as much as the new lines cost.

 

I agree, most people will tell you to go into the rad then out and into the cooler then return. If i were to do an auto I'd have a stand alone cooler.

 

Today I can say that shes all back together.
I did the stand alone trans cooler as you guys suggested. I'm still concerned about my cooler lines.
I wont get my *cough ''allowance'' *cough until Monday, so I have some time to look for ones that I like.

 

Yesterday, I bought 2 5' sections of the steel 3/16 hard line. I hooked it to the trans and I ran them to the new cooler that I mounted in front of the radiator. On a TH350 trans, dose it make a deference which way I connect the lines to the cooler? I'd like to hook the return on the bottom to make it easier on the fluid pump in the trans, but I think it gets around 45-50psi anyway.
I got tired of dealing with the PO's wireing nightmare, so I installed a new oil pressure gauge with a presser line to the back of the block. I also installed a new water temp gauge that reeds the temp without using any power. I converted the choke to a manual one and ran the cable to the dash.
I was giving the engine a good once over and noticed the ALL of my spark plugs where lose. I pulled them out and replaced them with new ones. We will see....The #8 cylinder plug had a bit of motor oil on it. All the other ones where clean. Thoughts?

 

Wont matter which way the lines hook to the cooler. It's not directional.
Oil on the plug can mean either rings going, or valve guides/seals.

 

Ok, thanks for the info on the cooler.
I'll pull the valve cover in the morning and check the seals, then do a compression check. I replaced all the seals and rings, but I hope I did not do something wrong....

 

So, shes back on the road for about 10 miles. I slow to a stop at a red light and it slowly sputers and dies. I crank and nothing... I crank one more time with the pedal matted and it starts. I limp her into a parking lot and pop the hood. I take a glance at my clear fuel filter and its empty. I pull the air filter and the carb is dripping fuel from the forward ventures like it did before.
I call my wife and get a tow home with my jeep.
I'm going to pull off the carb and check the power valve once more, as that was blown out last time. I did not hear it burp tho the carb this time tho. How would it afect it if I got the valve block off kit? Its a holley 600cfm with an accelerator pump and vacuum secondarily.

 

I wouldn't eliminate the power valve on a strictly street car. Make sure you're getting a power valve that is the correct size for a stock Holley. Should be around a 6.5 if I remember correctly.
Sounds like you may need to rebuild it, or replace it.

 

I picked up the power valve saver kit and the 6.5 valve. I'm going to use my drill press to install it, so after my in-laws take off, I get started on it.

 

PV rating should be something like 2 higher than idle vacuum. Not for sure but its on Holly's website.