It doesn't necessarily turn me off as a consumer, though I see through the visual pricing trick in those cases. $1999 is still 2 grand to me.

For pricing my products and services, it depends. I like keeping it simple for me, first and foremost, so my packages are more like $150/hr, $1500, $5000 in order to simplify the running of my business for me.

There are a few instances in another business I have where we price a webinar at $99 because that's pretty standard and easy.

What it comes down to, though, is whether or not you have something of value to offer. If you do, customers will be happy to give you $29 or $30 or $499 or $500. Because you're providing value to them. If you're not, pricing can't help you.