Something to call out here before we dive into it:

...[W]e’ve heard from so many of our users, particularly newer ones, that the learning curve is steep and it’s difficult to find ways to engage on the site.

This is orthogonal to reputation. Being able to participate on a site is a different problem than what the numbers mean next to your avatar and what you get for having your numbers grow.

Getting users to participate and feel like they're engaging on the site means that you have to give them an incentive to engage. A lot of people use Stack Overflow as a means to an end - ask a question, get a question, move on with their day. The folks who want to engage in a community may stay for longer. The folks who want to share their knowledge may stay for longer. None of this has anything to do with reputation.

With that bit out of the way:

What is really great about our reputation & privilege system? What do you think makes it great, and why is it worth keeping?

A lot of this boils down to familiarity, but it's really the sentiment that the system we have accomplishes a few things:

• Strong bands/divisions based on either participation levels or quality of answers
• Placing tools in the hands of power users, should they choose to use it, when they've had enough winters under their belts
• Something to strive for; while no one will really come close to Jon Skeet, they can at least shoot for the stars

What is broken about it, and why? Are there any solutions to it?

It is quite fragile, since it's the main measure of two things in my mind:

• How active you are, and
• How expert you are

To that end, these are the things that have broken it in the past:

• Giving questions 10 reputation, which inflates the amount of reputation that users actually get/earn from participating in the site
• Previous efforts which rewarded reputation in an unchecked fashion which were never recalculated (looking right at you, Documentation)

What other systems work really well that we could learn from?

While it's not perfect, I think the sentiment is that it's a more social variant of an Elo rating for everyone here. That is to say, the total reputation you have is a factor of how well your content is received against the wave of everyone else. This does make participation slightly daunting (which fine, you've caught me, I've come a bit full circle on this haven't I?), but it does mean that the system has a very explicit goal in rewarding those who are participating and whose content is comparable or better to others.

You don't explicitly state what your goals are for reputation, so it's not really feasible for me to say that something needs to change here. But I really don't think the system is particularly bad.

We just have to be very judicious when giving reputation out.

Something to call out here before we dive into it:

...[W]e’ve heard from so many of our users, particularly newer ones, that the learning curve is steep and it’s difficult to find ways to engage on the site.

This is orthogonal to reputation. Being able to participate on a site is a different problem than what the numbers mean next to your avatar and what you get for having your numbers grow.

Getting users to participate and feel like they're engaging on the site means that you have to give them an incentive to engage. A lot of people use Stack Overflow as a means to an end - ask a question, get an answer, move on with their day. The folks who want to engage in a community may stay for longer. The folks who want to share their knowledge may stay for longer. None of this has anything to do with reputation.

With that bit out of the way:

What is really great about our reputation & privilege system? What do you think makes it great, and why is it worth keeping?

A lot of this boils down to familiarity, but it's really the sentiment that the system we have accomplishes a few things:

• Strong bands/divisions based on either participation levels or quality of answers
• Placing tools in the hands of power users, should they choose to use it, when they've had enough winters under their belts
• Something to strive for; while no one will really come close to Jon Skeet, they can at least shoot for the stars

What is broken about it, and why? Are there any solutions to it?

It is quite fragile, since it's the main measure of two things in my mind:

• How active you are, and
• How expert you are

To that end, these are the things that have broken it in the past:

• Giving questions 10 reputation, which inflates the amount of reputation that users actually get/earn from participating in the site
• Previous efforts which rewarded reputation in an unchecked fashion which were never recalculated (looking right at you, Documentation)

What other systems work really well that we could learn from?

While it's not perfect, I think the sentiment is that it's a more social variant of an Elo rating for everyone here. That is to say, the total reputation you have is a factor of how well your content is received against the wave of everyone else. This does make participation slightly daunting (which fine, you've caught me, I've come a bit full circle on this haven't I?), but it does mean that the system has a very explicit goal in rewarding those who are participating and whose content is comparable or better to others.

You don't explicitly state what your goals are for reputation, so it's not really feasible for me to say that something needs to change here. But I really don't think the system is particularly bad.

We just have to be very judicious when giving reputation out.