What to sell and when? Struggling

[IR201]

How do you guys decide? It's easy for me if I want a new watch so bad that it forces me to part with something else right away. But I've decided there's nothing I'm really pining for that much, and I feel like my collection is a bit excessive now (for me, certainly people on here have a lot more).

But I can't decide what to part with despite weeks of obsessing over it. I go back and forth with no resolution. And even if I did decide on selling something - one of my 5 digits for example - since it is not urgent, what's the best time to sell - now or down the road a bit?

Kinda stuck. I know there's people who claim to know exactly what they want at all times (and belittle those who have some watch indecision). Power to them I guess. But for me it feels like I'll go to bed thinking one thing and wake up thinking another. Anyone have any tips and tricks to find out what you really want to keep and what you don't. I came up with this idea of imagining one of my watches got lost or stolen, and I got insurance money, then asking myself would I buy it back. Anything else like that?