Work out the reading order for a sprawling franchise

I want to get into Discworld and I don't know where to start.

Already read or watched: Only Mort, years ago, on a plane. Liked it but didn't chase down more.
What I want: the shortest path to the best stuff
How much I'm up for: I'll happily read ten if they're good, I won't read forty

Give me an order as a numbered list. For each entry:
- What it is, and roughly how long
- One line on why it's here at this point in the order
- Whether it's skippable, and what I'd actually lose by skipping it. Be specific. "Adds context" is not an answer.

Rules:
- The first one has to be a good entry point on its own terms, not just the earliest. If the famous starting point is a weak book, say so and start me somewhere better.
- Mark any point where I could reasonably stop and feel finished. People give up on long series because nobody told them there was an exit.
- If there are separate branches that don't need each other, say that plainly instead of merging them into one long list.
- Flag anything widely recommended that you think is overrated, and why. I'd rather have your honest read than the consensus list.

Then one line at the end: what I should expect to feel about a hundred pages in, so I know whether to push on.

What you get: A numbered order with honest skip notes, marked exit points, and a warning about the overrated entries.