Looking for my Goldilocks Personal Item/Daypack

Hi all, I'm on a search for the perfect airline personal item backpack that doubles as a daypack when traveling.

The MUST HAVE features are:

- Within generally accepted personal item dimensions
- External water bottle pocket
- 15 Inch laptop sleeve
- External attachment points for gear (molle, daisy chain, loops, etc)
- Suitcase handle passthrough

NICE TO HAVE Features:

- DWR
- External pocket or two

Currently I have the TravelPro Crew Executive Choice 3 Slim and it has all of my must haves except there's no way to do any sort of external attachments. Being able to use a carabiner to clip on some sandals, or a pillow, rain jacket, etc is missing.

For context, I travel frequently for business and tourism and take a carryon suitcase for my clothing plus this backpack as my personal item. Inside is my CPAP machine, camera, medication, headphones, and maybe a book. Once I reach my destination it gets unloaded and it becomes my daypack for light hiking and sightseeing housing things like my camera and a lens or two, jacket, and any souvenirs I purchase while out and about that day.

So far I've struggled to find anything better than the TravelPro. Packs from outdoor companies will often have things like the attachment points, bottle packet, etc. but they seem allergic to the luggage handle passthrough. More business-like or urban packs will do the passthrough but often go for a sleek minimalist design with no attachment points (like the TravelPro.