1. Yes. You have to organize your stuff and use it for your taxes. You have to give the IRS your log whether it is attached or mailed. You will wait a few years and see if they ask. The IRS has trained over a thousand agents in the last year or two on handling sch D issues and the logs.
2. You are right about adding a message and potentially flagging it: but, it can also be preventive measures. Personally, I would not add it but for some people, they feel better. It sounds like you are in my camp.
Side note: your issue is one that many are dealing with so the IRS may have to work out a method and your screenshot was brilliant. I don't expect you to have a big problem.
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