Bags
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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
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
I chose this over the 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.