Bags
I own all sort of bags.

My general carry around. You'll most likely see me with this.
I originally used the Peak Design Everyday Sling 10" but the hard surface makes it unnecessarily big when its empty. The compression straps are a joke. Also it didn't fit well when full with my previous iPad Pro 12.9".
Normally carries around my:
  • 900ml Naglene water bottle
  • iPad Pro 2018 11"
  • Wallet, keys, etc
  • If necessary, my small portable umbrella
Pros:
  • Small
  • Flexible
Dislike:
  • The clips, as they are next to the velcro, the velcro tends to fray the cloth attached to the clips

When I need to carry around my 15" MacBook Pro 2017. I used to use the Peak Design Everyday Messenger Bag 15" but my shoulder would start hurting after long periods of time. Also was difficult carrying in the iPad Pro inside as well.
Normally carries around my:
  • 15" MacBook Pro 2017
  • iPad Pro 2018 11"
  • 900ml Naglene water bottle
  • Wallet, keys, etc
  • If necessary, my small portable umbrella
Dislikes:
  • The clips on the side
  • The zipper for the front pocket keeps getting snagged on the top flap.
  • Holes in the zipper for a security lock.
Wish:
  • Side handle
I chose this over the Authority because I didn't want another compartment because I know I would lose things in it. I thought an additional compartment would make it too easy for me to stuff my bag with more stuff, and make it heavier.

My old everyday carry. I now use the Timbuk2 Classic Messenger.
Dislikes:
  • Hard casing makes it bigger than it needs to be at times. The compression straps are a bit of a joke.
  • Didn't fit my old 12.9" iPad Pro too well.

Dislikes:
  • Difficult to fit my iPad Pro 2018 11" and MacBook Pro 15" 2017

Pros:
  • Big
  • I love the way it can be attached to an airline roller so you can distribute the weight
  • I love the side handles
Dislikes:
  • Sometimes bigger than it needs to be
  • Compartmentalization for stuff is difficult
  • Zippers don't securely close at the bottom of the bag
    • Can easily open small holes and small items can drop out
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On this page
Timbuk2
Timbuk2 Classic Messenger Bag
Timbuk2 Division Laptop Backpack
Peak Design
Everyday Sling 10
Everyday Messenger 15"
Everyday Backpack 30L