"Here is a little thought experiment for those who don't "get it". Would you accept someone sitting in a parked car in the morning waiting for you to leave your house then following you to work. When you walk across the street they are right behind you following your every move and recording everything you do?"
I actually rather think you've missed his point, his point is that Microsoft is sending anonymous data back - i.e. data that can't be tracked to you. Someone following you to work by very definition can be traced back to you because it's you they're following and tracking.
I think there's a fair discussion to be had about how anonymous the data is, and something still irks me to this day about paying for a product and using my CPU power, storage, and bandwidth for their commercial gain, but I do agree with the GP somewhat that there's unreasonable paranoia about telemetry sent in this way in general. Personally I think there should be something more obvious in it for me if they want to collect this data - i.e. give me a free copy of your software if I'm a test subject and let me explicitly agree to that. Don't make me pay hundreds of pounds for software only to use my computing resources to profit off me even further without my knowledge or explicit consent.
A large part the reason I think that is because people seem to not care that every search they make, every site they visit, every service they use nowadays typically involves anonymous telemetry being connected (even if you block tracking cookies, your actions are still being tracked and measured server-side). People still use these services, yet when the same thing happens from an OS, or piece of installed software on a desktop, or phone, they suddenly take bigger issue with it, yet the data collected may be no less anonymous than the data they're handing over on a daily basis elsewhere.