1. If I am remembering correctly, when I ran the Space Age League, we used the cumulative 5-season W-L record to determine draft order, with the weakest team over 5 seasons getting the first pick and so on down, with the idea that while people might tank, no one would find it fun to tank for five whole seasons. I forget what we did for the first four seasons though.
2. I think Space Age used 35- man rosters, so the number of picks needed to fill that number, with IR/DL players not counting against the total.
3. Boston gets a third round pick, Chicago no longer gets its 8th round.
4. The "Not a problem" answer.
5. I guess in the end none, it's part of being in a progressive. But when you take over a team that was tanked by the previous owner it is a drag.
6. Mostly the same answer as above..but if the commissioner is convinced that the draft picks were purposely traded away as part of an intentional tanking and/or way of punishing a league the previous owner knew they were leaving, the commissioner should have the discretion to add a maximum of two additional draft picks in rounds where the picks were traded way, ideally at the end of the round, without the teams acquiring the picks losing out in any way.
7. Chicago gets the player.
8. If Boston notices the error during the draft they can keep the player, but only if it is before the end of the round. Boston will obviously need an additional pick (not in that round, but after their already scheduled picks) to complete their roster.
9. Tough one. Reverse the second trade I think.
10.I think Boston forfeits their third round pick in the following year's draft.
6.