So many great observations.

The value of Steem Dollars is most likely taxable income when it reaches our wallet from rewards (at the trading value if there is even an exchange to cash it out at this point).

Trading Steem Dollars to STEEM may be a like-kind exchange, but there are many tricky exceptions such as "reason for holding the asset" For example, even trading gold for gold under certain circumstances doesn't qualify for a like kind.

Typically, one would report a gain when they receive the Steem Dollars based on the US exchange value on that day (and the gain is the new basis); then when one sells the Steem Dollar for USD (or USD value of bitcoin/altcoin), another gain/loss occurs.

I share frustration with the lack of guidance, and I am passionate about trying to help the crypto community at least have some food for thought on the issues. I'm thinking about creating an excel template for Steemit users, and then hopefully take it further with help from with someone who would be able to load data necessary from Steemit or Steemd. It's a high ambition I know, it's something for the future.