Sometimes, it just depends on how much you LIKE a particular gun.
If that 4 inch Model 19 just feels right, and you LIKE it enough, you can get used to carrying it on a regular basis, with the right gear/clothing combination.
Another factor is how dangerous your part of the world seems to you. If things seem dangerous enough, unpredictable enough, then you can get used to carrying anything. Danger quickly negates discomfort.
But if the potential for a threat to your life seems very remote, then even a small/light weapon can become a hassle to pack.
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Trust, but verify - R. Reagan
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