They are all pretty much equal TBH. Comes down to which feels better in your hand. Maybe go to a shop and try the lastest base models from each of those makers and see which you like best. Whilst you wont know exatcly what the cameras you listed feel like, you'll have a good idea.
Try a Canon 550D, Nikon D3100 and not sure about the Sony. Those will be closest to the cameras you listed in terms of feel and operation.
Sony is a 2008 model but D3000 is actually a few month "newer" than 500D if my memory serves me right. We may need a bit more detail on what it is that you like to photograph or if you have any experience with any particular brand? It's always best to know what the camera will handle like in your hands so may be worth popping down to the local shop and try them there.
Also since you're buying second hand you could also consider Canon XXD series, 30D start from £200 going up to £350-380 for 40D.
At that level there will be very little to distinquish them. One may have more MP, one may have video or some other gimmicky featues, but I can pretty much guarentee if you had 3 images taken by each one, you couldnt tell them apart.
I have a Sony A100 and A200. I am happy with them as I used to have Minolta kit and the Sony uses the Minolta mount thus my lenses fitted it. But if I were looking for a digital body I would go for Canon or Nikon as the lens ranges are superior.
The question you should really be asking is 'What sort of pictures do I want to take?' this decides the lenses and then the that leads to the body you need not the other way around.
I like macro work and the Minolta 100mm f2.8 is a sweet lens and this meant that the Sony simply enabled me to continue to use my existing best lenses.
Second hand route isn't bad at all since you get more for your money and as long as you buy from reputable sources (like here) then you're safe as apart from shutter there's not much else that can go wrong. XXD series are a step up from XXXD series, they have bigger and stronger bodies that handle better for most people (unless you have freakishly small hands) and tend to have more features and options.
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