We bought our Oreck nearly 12 years ago (Aug 2000) and it is still going strong! We have a business Costco nearby and they sell the bags for less than anywhere I have seen. I do not know the price of an Oreck nowadays to know if it is within your price range, but averaging it over 12 years thus far certainly needs to be taken into account, yes?
The upright came with the canister vac and a car vac at the time. They all three are still in excellent condition. In the past 12 years, we have replaced bags on the upright and canister, one power cord on the upright (although, DH may have just shortened the original cord), and two belts on the upright. We use the upright at least twice as often as the canister and probably twenty times as often as the car vac. The Oreck has handled two different cats (one puked a lot, but had short hair and was declawed -- the other is very healthy, but has long hair and sheds nails a lot, too) and one full-time child (for 11 years) and part-time other kids (babysitting co-op in the toddler stage; many play dates, parties, and sleepovers in the school age range thus far) AND, most impressively, a lot of home improvement clean-up over the years.
We got a mini shop vac about 4 years ago, but still use one of the Orecks usually. (They are more convenient.) We got a Roomba on Woot.com for $155 including shipping and absolutely loved it! For 4+ years, the Roomba did the frequent vacuuming (maybe 3 times a week) of the main areas downstairs (living room, hallway, and kitchen). We replaced the battery once via Amazon, but have refused to do so again...the batteries averaged just over two years; something to keep in mind. YMMV
Edited by sunnysandiegan - 7/9/12 at 5:15pm