nsec.app itself doesn't work anymore for me. It always says "Something went wrong".

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Please try clearing the browser cache for use.nsec.app and then login back again or re-import the nsec. Looks like some local problem with your local database.

Are there any known issues with Amber login and it maintaining login?

I am not using Amber too often, last time I checked you had to setup the relay and notification service properly to make it reliable.