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I had the same idea. Winter won’t be a issue. Summer is where clothing choices will be critical.
I also considered using tape on the straps to help smooth out the lines.
I did read somewhere about conditioning your panels by rolling them up in various directions to increase there flexibility I guess. Need to look for that again.
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Realistically you only need a couple shirts to rotate through, unless things deteriorate to the point we're always wearing armor.
The pro-gamer move would be going now, in your winter layer clothes with the vest, and go to the mall to buy some shirts. That way in the changing room you can easily verify which shirts actually work.
Taping over the velcro or somehow smoothing it down, would be worth exploring. Gaffers tape would be a good option, as its designed to remove without leaving sticky residue, and has a cloth like feeling to it:
https://www.amazon.com/Professional-Gaffer-Power-Non-Reflective-Multipurpose/dp/B00GZE3UJ8/And like i said, experiment with the velcro tension. Took me some experimenting to figure out what works best with mine - turns out mine works best with one shoulder slightly tighter then the other.
In terms of armor break in, 100% would recommend, really makes it much more flexible. This is the exact process I used on both my Stinger II and older IIIA vest. Its a lot easier if you take the armor out of the vest; I tried to be lazy and it was much harder rolling up the whole carrier.
I also found wearing it around the house, and also driving in it, helps both with the break in and also familiarizing myself with the feel.
All in all though, I think you did really well for $300 with that setup. And I think you can imagine how much harder concealing a thicker (0.33-.35") IIIA vest would be.