This article will address why I choose the bags / tools to carry at any given time. This is not an article about what I look for in a bag (see this article or a more recent one about sling / cross body bags).
This is my current practice, and is subject to change.
In general, I want the biggest bag that holds the most stuff that will blend into my environment as effectively as possible.
95%+ of the time I carry my Adidas Rydell sling bag (the Capital is the current model). I can carry my second largest trauma kit inside, as well as my AR15 pistol in 300 Blackout or my Mini Draco vSBR. It blends in well in many environments, including downtown sidewalks, casual restaurants, big box retailers, movie theaters, and corporate headquarters.
The other 4.5% of the time I choose the Solo Active Universal Table Sling. I carry my MasterPiece Arms MPA 930SST vSBR inside, along with a smaller trauma kit.
The remaining time (very, very small minority, probably 5 times in the last 3+ years), I carry a laptop bag with my vSBR inside, usually my Mini Draco vSBR.
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