Form 5500 — at what point are you required to file, and what's the real penalty if you miss?

We just crossed 100 participants in our medical plan and are getting flagged that 5500 + Schedule A filing is now required. Our broker is offering to handle it for $2K.

For anyone who's owned this themselves vs. paid a broker: how much actual time does the filing take you? And for the people who've been late or wrong on a filing — what was the IRS / DOL response? Penalty letters, audit triggers, or mostly ignored?