It reduces confidence because warez is associated with running cracked software of which you don't know exactly what was modified/added/etc.

My how far we’ve come in such a short few years.

Eh, not sure what you mean, but yeah some DRM is obnoxious and almost spyware. Warden, World of Warcraft's DRM, is for example profiling your system hard.

It speaks to the priorities, attitude and / or the work ethics of the developers involved. I wouldn't trust people who care about using teenager slang and looking cool to write secure and efficient services that I could use in production with customer data. I may be wrong, but my confidence is still low.