When to sell Gen II and upgrade?

I do not recall seeing such a review, either. However if you look at p. 95 of the April 2011 Consumer Reports magazine, you will find the red/black circle charts showing the various trouble spots as reported by the annual survey of the magazine subscribers.

2G Prius for every year displayed shows "much better than average" as an overall rating. Compare to 2010 which is only "average". That is a significant drop and is probably related to the 2010 braking issues that required a firmware upgrade. Perhaps that is what firepa63 had in mind.

 

I have a II and prefer it to the III as well. I would keep it. If oil futures continue to climb, resale value will increase. And they'll be a lot more hybrids and electrics on the market in the next couple of years to choose from.

 

Like others said, reason suggests to keep the car. However we know very little of you to give an advice that will keep you happy. In a year the Toyota Prius family base package pricing will look like this:

Plug-in ~$28k (guess)
V ~ $28k
Gen III ~ $23 k
C ~ $19k (guess)
used Gen III ~ $16k
used Gen II ~ $12

I think it will be much better to buy a hybrid next year.