There should be a strip guide on your crimp tool, or an integrated stripper that cuts back the sheath the proper distance.
When properly crimped, the strain relief should latch while grabbing onto the sheath.
There are many slight variations to the connectors to handle different wire sizes, insulation thicknesses, and round vs flat. The contacts may be bifurcated to straddle solid conductors, inline to make maximum contact with stranded conductors, or slightly offset to handle both. These are important when you care about production-scale reliability, but aren't usually thought about too much when doing field crimps.