Ask yourself this:
Is your 500D broken or has some limitation that is preventing you with getting the photographs you want?
Unfortunately, our dSLRs are essentially disposable items (unlike the old film SLRs which you could keep using forever if you wanted to). Improvements to sensor technology and so on eventually drive most of us to upgrade our cameras to get the better resolution, noise reduction, dynamic range, ..., offered by newer models. I aim to hold onto my dSLRs for 3-4 years before replacing (hence my 40D purchased in 2007 will be replaced by a 5D Mk III whenever that gets released)
Rather than upgrade one generation in camera, and if there is money burning a hole in your pocket, are you better served by buying a high quality lens instead that will be usable from camera to camera in the future, and defer your camera upgrade into the future when the difference between the two cameras will be more meaningful?
Re the 550D vs 500D. This was pulled from dpreview (
http://www.dpreview.com/previews/CanonEOS550D/). None of these improvements would be compelling enough for me (but that is me, not you)
Canon EOS 550D vs EOS 500D Key differences
- Higher resolution 18MP CMOS with gapless micro lenses
- ISO 6400 no longer in 'expanded' range (12,800 max remains the same)
- Redesigned buttons and new movie/live view button
- Customizable auto ISO ranges
- Improved 63 zone metering (iFCL)
- 3:2 format screen with more pixels
- Improved movie functionality
- Slightly higher burst shooting rate (though buffer holds fewer shots)
- HDMI control (CEC)
- SDXC compatible