I deal with these circular connectors on almost a daily basis but I have no experience with the non-aviation ones and I would be interested in seeing the removal and crimp tools for these. They look ok from the picture ( metal body, etc)
As far as the commercial variety, we classify them by pin size: 20,16 and 12 gauge are the most common. Most connectors are all 20's or 16's or 12, although there are some lesser used mixed configurations. Some are pretty pricey and places like Newark and Moser sell them and have a good selection as far as circular connectors if you want top quality connectors.
I am guessing the generic China copies of the DMC turret head crimpers look identical and will probably do just as good a job at a fraction of the price.
Good crimpers will adjust to pin size as well as wire gauge size.
I don't believe I have ever seen a bulkhead connector that was not flange mount in some way. I would think a jam nut style mount could twist over time or loosen with vibration.
Aircraft wire is generally tin or silver coated copper and most common is 20,16 and 12. gauge. You will never use a larger wire than the pin. For example, if you want to use 14 gauge wire, you would use a 12 gauge pin and not try to stuff it into a 16 gauge contact. 16 gauge aircraft wire is probably equivalent to 14 gauge automotive wire in current carrying capability. They have similar size sockets/pins with smaller cups for different wires.
I don't think for automotive, I would hesitate on folding a wire over inside the crimp cup to get a good solid crimp.
I see very very few solder pins in connectors. They just don't seem to use them in commercial aviation, and if they do, its usually very small, low density connectors.
The aftermarket inexpensive connectors probably don't suffer from this problem, but some aircraft connectors are almost identical EXCEPT the keying. The part number will be almost identical except the keying in the part number.. This is to make them idiot proof when close proximity to each other. Some still manage to destroy them trying to mate them.
If you are concerned about moisture, first rule is to insert any unused sockets/pins into the connector even if not used, at least on the moisture prone side. This will help to seal out moisture and also you will have some spare pins handy if you ever need them. Boeing makes a green sealant for the rear of connectors that ends up the consistency of green jello, but it has been my experience that for the most part, sealing up a connector usually just traps water inside if it does get in. Connectors should be positioned where water intrusion will be limited, if possible.
I think to sum it up. The round circular connectors are cool, efficient, durable and extremely reliable, but can be very expensive and tooling can become an issue and if I didn't get take-offs for free, I would probably go with the plastic style rectangular offerings from Deutsch or similar with good weather proofing.