Definitely go with the trifurcon contacts: 08-52-0125 as they make three points of contacts to the pin. Very solid and reliable connection to last longer.
Unfortunately you did spot one downside of crimped connectors but honestly it's that much of a downside if you take your time. Take a look here to get a good idea of how to tackle looped connections with crimped contacts:
http://www.pinrepair.com/connect/#looped
The article recommends soldering but IMO crimping and soldering don't go together. So note this. Since you'll be "doubling up" wire I would grab some of the bigger gauge contacts in addition to the smaller ones: part 08-52-0072 at GPE as that will nicely fit two wires. That way you have contacts to fit 22-26AWG and 18-20AWG and you can use the 18-20AWG contacts for doubled up wires.