We all have sentimental items. Saying goodbye to those items can be difficult. A prolonged goodbye is not a bad thing. It may take more than one pass to be ready to let it go. Start with the least sentimental stuff and work your way towards the things that hold more memories.
A maybe box is a good option especially if you need some time to think about your decision to let go or not. While you’re deciding remove those maybe items from your every day living space.