It's really a matter of what you are doing with the truck vs. what you feel comfortable paying to mod it out and how far you want to go.
The TH400 is a pretty strong and very reliable trans even in stock form, but sadly missing a 4th gear. You can keep the TH400 and go with a Gear Vendors unit, but that will set you back about $3K from what I estimate.
The TH700R4 is a standard level transmission that can be built up, but to make it as semi-reliable as a TH400, you're probably looking at $2200 - $2700 depending on how far you go. In my opinion, the 700R4 will never be as strong as a 400.
You can go the 4L80E, which is a very strong trans, from what I am told, it is basically a TH400 with a 4th gear that is electronically controlled, so it will need a computer module to run in a truck without an ECM, which runs about $600 -750.
Now the only thing I didn't mention is what else is needed to make the change, like driveshafts, shaft yokes, U-joints and so on. When you start changing rears and front axles with different trannys, you may find that there isn't a direct bolt-on conversion from one unit to the other.
With any of these trannys, a good cooler in addition to the in-radiator cooler should be always considered, standard if planning on any type of towing.
As for the 14-bolt rears, most of those were either 4:10 or 4:56 ratios, I'm sure there are more with lower ratios but you would need a RPO guide to determine what ration any rear has if coming from a boneyard. Either that, or you have to crack the diff and check the numbers on the ring gear.
Good Luck!