Prices are regional and based on sq ft, so who knows. Drip edge may or may not be required, I would go with gutter apron. "Two flashings were not caulked properly." - they probably were but 11 years later - ... Tell this to your roofer. Most of those small things.

Find a reputable roofer in your area and ask. I go on Nextdoor, and read reviews and recommendations. That is how I found a great roofer. He is honest, he photographs the trouble spot, tells me how it will be repaired, and what it will cost, etc.

We have used him a few times, and he must like us too, because when we had a leak in a rainstorm, he put us at top of his list to visit right away.

As a homeowner, I like to build a relationship with quality people like this roofer. I recommend that, vs. getting a low bidder. You will just have to go through all that again with the next roof issue.