If your holes through studs (and especially metal ones without proper grommets) are tight, it's easy to score the tubing.
Nicks or scratches on the ridges of fittings can be problematic. Improper placement or crimping of the ring can allow it to leak. WIth a go/n0-go tool, they can wear out after time.
WRT crimp versus expansion fittings, on expansion, improper placement of the ring can be a problem as can not inserting the fitting properly into the pipe.
While pex itself usually won't be damaged by freezing, that does not necessarily apply to the fittings, and UV exposure can damage it.
Crimp rings are trying to compress the tubing so the ridges can make a seal, so if it isn't tight enough, it will want to spring back to its original shape. That feature is what makes an expansion fitting work...the natural springiness of the tubing wants to evenly clamp down onto the fitting. PEX-A is the only version that that works on, as it has the most cross-linking, so has the best (strongest) memory of the original shape. The other types would tend to shear those bonds if you tried to expand them.
It does take good workmanship and a little knowledge to do this.