You´ll always be able to sell/tradein the 9 and by the new shiny

I wear it when I´m at work or when I´m out. I also wear it through the night for sleep tracking. There is zero reason for me to wear it all day, I dont like having anything on my wrist while I´m at home.

Gen 1 Ultra is perfectly fine. The updates on the 2 are incremental.

I put it on the charger 1 or 2 hrs before going to bed. The only difference is I never rely on auto updates on any of my devices. I manually request the update(if there is one) and then plop it on the charger.