Making my Dart road trip worthy

Hi everyone,

I've got a few questions about what I should do to my Dart to make it road trip worthy. I want to take my car on the Hotrod Power Tour, or at least a leg or two of it, and I am not sure what should be looked at and replaced to take on such a journey.

My Dart is a 1969 340 Swinger that I got running a year ago. I had the heads off, replaced the freeze plugs, new head gaskets, new intake gasket, and rebuilt the carburetor. It's got new wheel cylinders, new drum brake shoes, new tires, the gas tank was removed and cleaned, but when I parked it after the last car show it dumped all 7 quarts of transmission fluid out of it.

My plans were to take the engine and trans out this spring and replace the oil pan gasket, rear end gasket and fluid, and figure out where the transmission was leaking from (unless someone has an idea already) and any gaskets/seals on the transmission. Wasn't sure if I should/need to replace the rear main seal, timing chain and gears, mechanical gas pump, or anything else I should look at while they are both out.

Sorry if this sounds like a newbie question, but I appreciate any feedback/help on my question. Thanks Everyone.