About the tax planning+timing issue. You just don't get it. Normal people already have no incentive to use Bitcoin and now they will really stay away from it. Why fuck with the hassle? Most people don't even know what a Schedule D is.
New software? Have you tried using H&R Block? I do every year, and they are the experts on simplification. My ex can't figure it out. I have to do her taxes this week.
I'm sorry but this is nonsense. For years people were required to declare and pay state sales tax on everything they bought from Amazon.com. Guess how many people stayed away from Amazon because of this? None. Either they did the accounting work or they just fucking ignored the IRS. Eventually Amazon was pressured into collecting the tax because the state governments had no way to enforce it.
I suspect Americans will do exactly the same with bitcoin CG that they did with Amazon state sales tax. It will be an inconsequential amount for 95% of users, they will ignore it and the IRS will do jack squat about it. It will cost more to audit than the revenue it will bring in.
BS. That was sales tax and Amazon collected it directly on checkout. It was no hassle at all.