I like the cut of your jib. Some of the most vocal complaints are things like someone holding a cabin or other piece of land for an extended time, and then having to claim the gains in a single year. Especially in cases like an inherited cabin that’s held for 30 years then passed to next of kin so a particular owner never actually paid or was paid for the property, but probably did spend as much on maintenance over that time as their assessed gains. Spreading those gains across multiple tax years that have already been assessed would seem fair(letting them claim the gains at a lower marginal rate by spreading it over multiple years) though administratively difficult. I would also like the idea of putting in a lifetime exemption around the $250 k range which would make a big difference for those who might only ever pay capital gains due to that one property, but not really affect those who make most of their income as capital gains.