Ducati manufactured many variants of 999, each with its varying levels of desirability. That said, I don't believe any model 999 will ever be worth more than it originally cost. The best you can hope for is mild appreciation from it's already depreciated current value, possible as some said, to keep pace with inflation. Definitely will lose money if you choose to ride it since maintenance and licensing and insurance fees will eat up any "appreciation".
Anyway, like I was saying, 999s come in many different flavours. By far, the most desirable are the WSBK homologated R models, of which they made limited quantities every year. It had top-shelf Ohlins suspension, Termignoni exhaust+headers+ECU upgrade, carbon fibre body panels, special paint/decals and the piece-de-resistance: the uber-go-fast-exotic-materials-made engine that made more hp than the base models. Of the 999Rs, there are three paint jobs, the base red, Fila graphics and the most desirable is the Xerox 999R that won a few WSBK championships. Next step down is the 999S with the upgraded suspension and white number boards and then the base model. Going off memory, brand new, R models were around $55K CDN, S was $26K and base was $22K.
Then there are the monoposto (single seater) vs biposto configurations (999Rs only came in monoposto). Even though both configs cost the same when new, monopostos are more valuable today. They also had a cheaper 999 Dark model with a matte black finish instead of the gloss black base 999. Although these were made in smaller quantities, I don't believe they are worth more, because they were a budget 999 to begin with.
To muddy the waters even more, the 999 got a refresh for the last two years of production, 2005 and 2006. The base 999 got most of the hp bump of the previous version 999R engines, even though it wasn't the exact same materials. Also, it got an updated fairings and many people think it is the better looking of the two versions of 999, and the used market pricing should reflect that.
I haven't checked lately, but as of a couple years ago, 999 prices have stabilized. 999Rs are around $15K CDN and should hold their value/slightly appreciate *IF* they aren't ridden. The thing with the 999Rs is that they are individually numbered (x out of 500), so it's easy to track them on Internet registry and classified ads. There's a janky 999R going round in Western Canada that's changed hands at least 4 times already (at least that's documented) and the current owner is asking more than what he paid for it, despite putting a few thousand kms on it. It goes up for sale every spring, but no 999R collector is touching it, because its history is so well known.
I don't see a lot of 999Ses on the market, but the base 999s should go for around $5K-7K, depending on year, mileage and condition. I wouldn't pay more than $9K for a pristine 2006 999 monoposto with low mileage.
Buy a 999 if you want to ride it. They are fantastic riding machines. But I don't think you're going to be able to wrap it up, store it and make money selling it in the future.
If you want me to take a look at an ad and give you my opinion, PM me.
But be warned, if it's a good deal, I will buy it out from under your nose.
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