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Big decision....

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OP is indeed rolling the dice. No way for sure to know in advance if continuing to drive, or buying another is the best course. Time will tell.

Knowing that a serious refresh (Juniper) is coming in the future just adds another level of nailbiting.

OP also should consider the fickle nature of Government rebates. Those tend to come and go. Buying when there are significant rebates can really tilt the scale of affordability.
Only 5k in Ontario..... Actually kind of hoping Libs or NDP get in so maybe we have a provincial rebate as well, like QC does.
 
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Idk..... Will cost me about 35k cdn after tax to go to a new Y. Tesla trade ins are horrible, so I'd have to sell privately. I'd also kind of like to wait for the Y refresh too, should be many improvements. But, I'll be really kicking myself if my pack or drive unit fail.
You have free Supercharging now & TSLA has been offering 'transfer' of this & FSD until the end of March '24. They will likely repeat this offer again. "Juniper" will be in Canada by year end ( we think/hope ), so possibly roll the dice & go for the new Y then. There is that $5K rebate to consider too! Lifetime Premium Connectivity seems to 'go' with a trade.
 
You have free Supercharging now & TSLA has been offering 'transfer' of this & FSD until the end of March '24. They will likely repeat this offer again. "Juniper" will be in Canada by year end ( we think/hope ), so possibly roll the dice & go for the new Y then. There is that $5K rebate to consider too! Lifetime Premium Connectivity seems to 'go' with a trade.
Yes, I'm hoping if I wait long enough I'll be able to transfer my free supercharging. No FSD for me, heck my S doesn't even have basic AP lol. I'd love to transfer my premium connectivity too, but that's not likely.
If I bought now, there's free SC, 5k rebate, and the Y has been marked down 4k in Canada too. Same price as a 3 right now. I'm pretty sure I'm gonna roll the dice and wait though.