On the fence. Didn't need the extra power on the LR, but did add the performance upgrade (software) to compensate. The biggest issue is ride quality - I swear that the Performance had a better ride. Still prefer the LR overall. Of course, other regrets will always happen down the road as Tesla has added things since our purchase - heated steering wheel, revised centre console, and HEPA filter. You might even end up with Matrix headlights (unclear whether they'll be on the LR for the long term).
Unclear about winter problems - there was some issues supposedly due to software (fixed) that caused issues with the heat pump. This year is probably the year to see whether there's any impact from it.