My guess is at least another two or three years. This is a very good little machine which is already incredibly useful and whose usefulness and functionality continue to grow.
Will keep it until it breaks.. i might get another similar machine if it comes. But then it will need a better cpu, rootfs and screen size of 4" with at least 1050x620 resolution.
For as long as there gonna be software upgrades.(don't care if they are official or unofficial) I don't think of my n900 as a cellphone anymore. It's a mini computer. And I don't upgrade my computers very often. There is one question that comes-up in my head: do we really need a faster mini-computer ? I am sure there are people who do need faster cpu. But for me it's more than enough.
I just picked you the galaxy s, but will still keep my n900 and use it over wifi. The n900 works great as a computer which is why I wanted it, not so good as a phone.
I'm very happy with my N900 and hoping to keep it for a long time, so I'll keep it until it breaks (USB port seems to be the Achilles' heel for this device)