It’s always bette for your reputation to cut a product entirely, than to come back and say it’s $1000 per support ticket when support tickets were previously free.

Would it be bad PR? Then it could also make enterprise customers worry about the same happening in the future.

Love these strategy discussions

Because you want to make a product that doesn't look silly / is worth all the effort to maintain it.

Having an noncompetitive product means fewer and fewer customers so the cost keeps going up per customer.

It also looks really bad. I know when I'm shopping around if I see sticker shock for some service even when it isn't exactly what I"m buying that is a big turn off for me as I assume that's how they price things ...

That only works out, when price matches customer expectations. Aren't you ever been position, where customer insist to get price offer for something ridiculous? Those clients always act offended, when you finally give them price. Even when you previously are communicating out that this is going to be really unreasonable, no point for calculating exact offer.