For my re-wire plan i decided to run the wires myself. I want my power panel inside the glove box and the painless kits are designed to have the panel in the left side (what I have read). I also just hate to chase ground faults as well as sand off beautiful paint and introduce rust in order to establish good body grounds. So for me I decided to run a ground wire to each light, etc. This adds one more hole for each plug. So what was a single wire connector is now a two wire, what was a three wire connector is now a four, etc. Handling the wire gages is a different matter. Rather than have three different gages to the rear and so on I will use the largest gage and make all wires that gage. Lots of extra cost I know, but must less different things to buy.
In your case Joe, you already have a harness so you need to look at each wire end and figure out the gage and number of wires. Write down how many of each number/size combination the make the order. Another option would be to buy a bunch of single wire connectors of different gages and just do singles. Kind of like the stock configuration. I wish we had a local supplier so you could get everything you need in one retail location, but...
So, terminal size refers to the wire gage supported by the terminal. Like 14 gage or 18 gage. The seal is a rubber piece that goes over the wire before you crimp on the terminal. It gets pushed into the back end of the plug after you insert the terminal in the plug (there is one that goes between the plug halves too). This makes the water resistant connection. A plug assy will accept different gages of wire. You need the proper terminals and seals for the gage. You can't use 10 gage wire with an 18 gage terminal and if you used a 12 gage seal on an 18 gage wire you would not have a sealed connection as there would be a gap between the wire and seal, etc.
Does this all make sense? Another thing I have read, and will take the word of others on it, is that once you insert a terminal in the plug shell you can't remove it. They do make removal tools, but I don't know how well they work. So, do it right the first time
Some online retailers only sell the weatherpak connectors in bulk and some in sets. I bought from a place that sold them in sets. So one set included both halves of the plug, all the seals and terminals. I had to select the number of wires (2, 4, 6, etc) plus the gage. I can look up who I ordered it through after I get home if you want.
Let's talk offline if you want more info.
Steve