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?
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Does this happen in every older save, or only one specific save?
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Does a brand-new Bliss Bay save show the updated assets correctly?
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Screenshots of Dowon showing the update option, and Bliss Bay missing it
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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.