Relying on a CSS hack means two things could possibly happen:
- A patch or update could fix the hack you're relying on, breaking your site until you find out about it
- Future browsers could also have buggy reactions to the hack, making your stylesheets unstable - you would need to remove the hack to fix for the newer browser and find a new workaround for the old one. Again, your site would be broken until you find out about the problem.
Either way, the safest thing to do is use standards-compliant stylesheets and conditional comments. By definition, support for these will only get better with time, so you are essentially future-proofing your site.
If you're especially concerned about the overhead of an extra stylesheet for certain browsers, consider putting them inline. Your overrides should typically be minimal - 90+% of styles should be shared across all platforms.