Hi Dave,
No, you certainly don't need all those tools. The list is different manufacturers of the same products. There are others too.
With insert-extract tools and crimpers you select the correct size tool for the size of the wire and pin or socket in the particular connector you're working on. The numbers "12", "16", and "20" assigned to the tool indicate the connector pin or socket size, and also the wire gauge size intended to be crimped and/or soldered in them. Wire in Cannon plugs is generally not crimped into the pin or socket --- solder only. With Douglas and Packard connectors I both crimp (first), then lightly solder. As mentioned, excellent durable results. Use a little alcohol to clean them up, then a slim coat of No-Ox on the mating surfaces and it's good to go for a long long time.
Those 3 size tools are most common in my experience and that was the extent of my research. I didn't research M38 or M38A1 tech manuals to determine where every Cannon plug connector is or what sizes they might be so I apologize if I confused the issue. It's certainly possible that every connector on these old gals is size 12. My M38 is converted to 12V and the only Cannon plug on it is the trailer receptacle (size 12, which accepts the 14 gauge wire used for lights). You can use one wire gauge smaller (for example, 14 gauge wire works in a size 12 pin or socket). Shouldn't do that on aircraft or the Space Shuttle, but ground vehicles is no issue.
If you do some searching (with patience) using key words like "vintage military crimp tool" you can usually turn up the exact same crimp tool that Wes has posted photos of many times throughout the forum, sometimes for a reasonable price. Unless you're hard over about using period-correct military vintage tools or building a show queen, there are many others that all do the same job equally well. The intent being a sound mechanical bond. I use a Sta-Kon tool myself.
I hope this clears things up. My apology for the confusion.
If you can't extract the pin or socket from the rubber block it's embedded in (inside a metal shell), how can you repair it?
For the curious:
https://www.sanchem.com/electrical-cont ... icant.html 
Ron D.
1951 M38 Unknown Serial Number
1951 M100 Dunbar Kapple 01169903 dod 5-51
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