I have taped and painted trim.
Tape gets tricky, especially with compound curves and right angles.
Paint chips. There is always one freaking spot that doesn't get enough sanding or enough cleaning. Usually dead center at the top of the windshield, where it is most visible (and hardest to touch-up).
That said, the last time I blacked out chrome trim I used a flexible finish - figuring it would be less prone to chipping. I think it is marketed as tool handle coating. Comes in dip cans and rattlecan. That was two years ago. Hasn't chipped, cracked, peeled, rusted or faded yet.
I figured I could confess that here without being mocked or scorned...
Attached is a pic of the car. The hassle that went into trying to get a decent paint job done on that car is the reason I'm reading this forum today for the others in the stable. Never again.
Roll on, bruthas....