It might help your mental association process to paint your sample bolts and their corresponding wrench with bright colors. After a while it will be "oh, that's a 1/4-20 screw, they're yellow so get the yellow wrench". In fact, didn't some of the older T-handle sets come with different colored handles?
I make this suggestion because the colored socket sets sold by HF have helped me with your exact problem when it comes to socket selection. I now know that the bolts on the rolling table are purple and the ones on the hold-downs are burgundy.
The T-handle wrenches that have a hex driver sticking out the side of the handle simplify the situation for non-captive screws. Simply press the screw head on the exposed bits until you get a fit, then pull that wrench.

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