Unless I start a completely new game, the world assets stay on the older version and don't update.

Thanks for narrowing this down. Since Dowon has the street lot update option but Bliss Bay does not, this sounds less like a local install problem and more like the save migration/update option was only applied to Dowon (?)

[Please fill the form about your specs, mods platform etc to help the team help you]

Also, would you mind adding this info/ details for the devs?

  • Does this happen in every older save, or only one specific save?

  • Does a brand-new Bliss Bay save show the updated assets correctly?

  • Screenshots of Dowon showing the update option, and Bliss Bay missing it

  • Your save file, if possible

Have you check if verifying the files through Steam help?

This may need a dev-side fix so existing Bliss Bay saves can receive the street lot/world asset update without forcing players to start over.