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That's a hard question as it's different for everyone. I'd pull the pony out and have it around you for a while. Maybe on the dinner table, or near your laptop, or wherever you spend a lot of time. Even at work if you have a workplace where that might be appropriate. Give the pony a chance to really grow on you! If you feel you love her a little bit more after having her near, then you'll know it's not the right time to part with her just yet. And if, after a week you still don't feel any attachment, it's pretty safe to say you won't miss her, then you can go ahead and sell without regrets.
If you are concerned about pony value like it's a stock market, hang on to them. Rare g1s likely still have a ways to go for a price increase. I wouldn't sit forever (if you are totally sure you want to sell) though. These are important because they are our generation of ponies. There is no guarantee they will act like a normal antique and be worth triple or quad what they are now when we're old 'n wrinkly.
I try pretty much the opposite of what Daffodil suggested, take it out of sight, away from the collection. Box it away somewhere safe and try to see/feel if you miss it at all. If not then let it go! I box my questionable collectables up so theyre ready to ship off if I decide to sell them, and just dont tape them in. Leave them in the closet for a few weeks and almost always wind up listing them! Im sort of a compulsive buyer though, so I need turnover to make space on my shelves and in my wallet
If I need the money, I sell them. If I'm okay money-wise, I save them to trade for something or a couple somethings I might really be after.