I am embarrassed to report that I failed to notice the attachment in your question. For some weird reason I tend to skip over some details. This has led as you may notice to extra frustration on my part.
To answer part of your question - "Does this sound plausible to do in VB macro in excel, python or VBscript" - Yes.
I'm still not 100% clear on what you want. "Randomly picking location "Four" would yield the locations of 7.1, 100.3, 105.3 and 106.3". By what magic?
Let's choose location 1 as the starting point. You would take row 1 in the matrix, examine each of the other 225 columns, extract those which are > 16100 into a list.
Maybe I'm missing something, but doesn't that just amount to examining each cell in the matrix, picking those > 16100 and putting them in a list along with their coordinates? That is a total of 25312 comparisons, takes almost no compute time to rearrange the entire matrix.
If that is all you want that is trivial. Why all the concern about random and 50 runs?