Hello Hexcede,
Thank you for your well thought out post. First and most importantly, we are not trying to punish the use of Wine.
Our Windows 64-bit client is in some regards quite different from the 32-bit client. We are currently gathering telemetry to analyze and hopefully fix existing issues and prevent future ones from popping up. For this process to work, it is of utmost importance to collect data from the indented target operating system. You will also find that we blocked the usage of VMs for the very same reason.
I hope this clarifies some of the thought process behind the blocking of Wine. As MrEaker mentioned before, Wine remains a priority for our team, and we are certainly not deaf to the voices of our community.