Hey, sorry, I've only just seen this thread now, but when I was firs looking at geting a DSLR about 25 months a go, I went through a similar process.
In the end, for me to came down to the 50D and the 550D (which was fairly new at the time).
In the end I went for the 50D, and have never regretted it.
The main advantage of the 550D was the extra mega pixels, and the fact that it it did video.
However, the 50D is a far superior camera when it comes to ease of use. One of the biggest differences for me, which is not obvious until you actually use it is the face that XXD and above cameras use a penta prism view finder, as opposed to xx_D models, which use Penta mirrors. Basically, a penta prism is far easier to look through, and it is brighter and clearer. This is something I'd reccomend you pay particular attention towhen trying cameras out. Another advantage of the XXd cameras and above is that they have far better autofocus systems. How important this is to you depends on what you want to focus on.
You can pick up a used 50D in NZ for 800-900 NZD. I'd reccomend looking at it....
A few more general pointers, if you are concerned about weight, then a micro 4/3rds system would be a good option to investigate. The main reason I love my DSLR is that it offers speed I've never found any P&S coming close to matching, as well as the ability to blur out of focus areas.
Finally, I disagree re the stylish bag comment, although I must say I'm not the most stylish person. there are a number of online companies which offer what I consider to be stylish bags (One example:
ONA | Shop), but they do tend to cost more.