As per the
datasheet:
Applicable wire: Conductor size/ AWG #32 to #28
Insulation O.D./ 0.38 to 0.63 mm
You can find 0.55mm 28AWG wire on digikey, its not the cheap PVC stuff you are trying to use, usually FEP or ETFE or something, as its tougher in that smaller diameter.
For the crimper, there is one on ebay for ~$200, seems like a good price. Or consider getting a quote from a cable manufacturer.