They are up already. I bought my 09 pack 4 prius @ 18,xxx miles in December, and a similar 09 (with over 57,xxx miles) is $19,500 8 weeks later it was totaled and i replaced it was a 08 Touring pack 5 @ 30000 miles and similar 08's are up more than $3,000 above what i paid. This is comparing the exact same dealer by the way.
You invariably lose money trading it in but even if you're a capable seller privately it doesn't mean you want to do it. I've sold several cars private party and hate it every time. A huge number of people never show up to look at it, others waste your time, ask if you can take payments, ask if you can hold it for a while, low-ball the ever living heck out of you, it's really a very irritating process. Of the four I've sold two were significant hassles, but they were relatively cheap cars (1400-5500 asking price), so I think they drag out, frankly, more desperate people. I'd be inclined to simply eat the $500-1000 next time I get rid of a cheap car and trade it in. I almost did that recently. Trade in vs private was maybe $1000 difference and worth not playing around with it. Kept the vehicle for now. Also, at least on craigslist, people want the deal of their lifetime. I've seen cars on there very cheap trying to get sold for months. Also, if you live in a high-tax area, trade-in works beneficially for taxes and private party won't allow it, so if you trade in a $10000 and buy a new vehicle at the same place you may save, say, 8% in taxes or $800 because the final taxes are based on purchase minus trade-in. That makes things more attractive.
CarMax? What planet are you from? Tralfamador? You can buy there at reasonable prices, but try to sell them a car and their offer will be laughable. They offered me $12k on a very rare Audi S6 that was worth more than $20k. They claimed (after their guy inspected it) that it had prior body damage and other problems and they'd have to send it to auction. TOTAL BS! The car was near perfect. I ended up getting $21k on a trade on our Lexus RX400h.
I've had three cars appraised at Carmax potentially to just sell outright. Two of the offers were ok and I did consider them but one was so offensively, outrageously low that I emailed their office afterward. It was way below any kind of a market value. Some of the cars they sell are at ok prices and some are disgustingly, sickeningly overpriced. I think in a way they are like Walmart, which normally has good prices but sometimes inflates them (for example try and not pay through the nose for coca cola--good luck, it's always crazy expensive at walmart). I normally find at least for buying a car that local used car dealerships are the best way if you don't want to do private. A one or two guy operation normally have pretty competitive prices. Trading in is always hit or miss anywhere, though.
Used Prius prices are definitely on the upswing. I'd much rather be trying to unload a used Prius rather than a tub 'ole guzzler! I wouldn't say Prius is an investment, but for sure, the depreciation rate is slowing way down.
Craig I tied you into a Gentex 536 install. Did you do this? I have a lead on a 536 coming from a KIA that I am trolling for. Any info that you can add will of help. Bill
I bought my car new at 23000 (pkg 2) when it c ame out 1.5 years ago. I was offered $21400 on trade in before negotiation. My car has 39K miles. The funny thing is that you could have gotten a brand new pkg 2 in December for $20700!