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Roadster: Which is worth more on open market? BRO OR Upgraded Battery?

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Unless you are "hard up" for the money (which I seriously doubt) I'd say keep it, exercise the BRO to 3.0 at the last minute (year 10) since you won't be "relying" on the range of the Roadster in the meantime and then perhaps sell it if it is still your desire (and you've learned it won't be used). I don't know the future but I think the Roadster prices are about as low as they really ever should be right now, I'd anticipate getting either the same or more money out of it in the future. I think in the very long-term future you'd be looking at significantly more money as it would be a collectible...

If you are hesitant to waste the "good" battery you have why not offer to do a core exchange with someone who has a junk battery and then get your 3.0 upgrade right after the core-exchange? Unless Tesla intends to continue to reuse the old battery cells (which I'd imagine they would only do if the customer is having replaced under warranty) they will be throwing them all in the trash/recycling bin anyways. I'm sure you can find someone willing to throw at least a little coin your way for that exchange; I know I would...