New 69 Chevy C10 owner, a couple of minor issues

[alabbasi]

All, I bought a cheap old LWB 69 Chevy C10, LWB in order to replace my old 73 GMC which was stolen last January.

The truck ran but had a huge oil leak and no brakes and a non working transmission. I've been working on this truck in order to make it road ready. The oil leak actually turned out to be a transmission leak which I addressed by installing a new filter and gasket. The dip stick was broken so I replaced it with a new dipstick and tube. However, I'm not able to seal the dipstick which will drain the torque converter over night. I need to figure out what to do here.

Second issue has been brakes which i've rebuilt, but have been unable to bleed. I"m down to the brake hoses and the the master cylinder.

The truck has rust and dents. The PO tried to repair the rockers using sheet metal and sheet metal screws so I need to figure out what's behind it and then turn it into a rolling restoration.

This truck has 4 wheel drum brakes with no servo. How safe is it to tow with this setup?