For 1: you should already be able to add a milestone which has tax consequences; there's an option on milestones that lets you redefine the overall tax setup wh

For 1: you should already be able to add a milestone which has tax consequences; there's an option on milestones that lets you redefine the overall tax setup when the milestone occurs. 2-7: all great points; I'd love to add more strategies over time to help optimize scenarios like these, though I'll have to think carefully about what can be generalized and what is strictly US-specific. Thanks for writing these up -- I'll be looking into them in more detail :)