Perhaps move this to Technical Discussion section.
Since you're not doing any tests, then your starting point, like on any topic, should be to read up. Start with the most obvious: the whitepaper:
https://bitcoin.org/bitcoin.pdf.
There've been lots of papers discussing Bitcoin privacy, particularly related to so-called blockchain forensics, used by enforcement agencies to track down (with great success) illicit activity using Bitcoin via address/tx association and following the blockchain trail. Here's a very recent study:
https://cdn2.hubspot.net/hubfs/3883533/downloads/Bitcoin%20Laundering.pdfHere's another from last year co-authored by Maxwell:
https://eprint.iacr.org/2017/1066.pdf looks at improving Bitcoin privacy. There was another by same co-author, can't recall where though.
Lighter stuff: you might want to read about several techniques used to enhance Bitcoin privacy, including mixing/tumbling, certain basic behaviours.
Thanks, I'll be reading these articles in a while. In the (unlikely) event that I perform a test, are there any widely-recognized softwares that can be used to simulate/attempt to crack Bitcoin cryptography?