Answers to your questions:
1) A lot. I'm not sure I understand what "workshop publication at a top-tier conference" means, but if it's a workshop associated with a conference, it's the reputation of the workshop itself that matters, much more than the reputation of the conference.
Having said that, what your letter-writers say about your work matters more than the quality of the venue. The quality of the venue loses its importance if your contribution is genuinely wonderful enough that (1) your letter-writers rave about it or (2) someone on the committee reads the paper and sees that it is good.
2) Yes, it will hurt.