Huh- I always thought crimps were desirable for aircraft wiring because solder was more prone to vibration failure...? I do know that in the A/V world, for rides and other things that move a lot, crimps, or better yet, screw terminals are usually used whenever possible for connections.
Regarding which is easiest to do (solder or crimp'n'insert): I'm pretty good at soldering, and generally don't enjoy crimping pins (on D-subs and other small connectors). Especially if you have to remove any pins because of an error- even with an extraction tool, it's a PITA.
BUT:
Solder or crimp, just remember your male/female pinout for D-subs... the little numbers on the block are hard to read, but the way I remember it is:
"From behind, the female looks correct".
In other words, with a D-sub, when you view the pins from behind the connector, the pin numbering sequence starts in the upper left corner, and you read the sequence left to right in each row (pin 1, pin 2, etc.). With a male, the layout is reversed (duh): starts in the upper right corner.