triggerfinger - 3:51 pm on Jan 11, 2011 (gmt 0)
You should optimize your META description for it's use in Google's "Snippet", which can improve click-thru-rates for your site's in SERPs. This should also focus on accessibility, as people with screen-readers and other alternative viewing methods will have proper access to your site.
H1's are semantic markup, meaning they should define whatever the first heading of a page is (think of a Newspaper or Magazine layout). This is also used for accessibility, especially mobile, making it easier to scroll and browse through your page.
Title tags are still the top relevancy indicator for Google's algorithm, so special concern should be given to optimizing the Title tag for keywords, etc. This can be done concurrently while also providing a good user experience, focusing on branding, accessibility, etc.
Focus on these things, and you should perform well in search engines. I don't believe having a H1 tag similar to a title tag, similar to a meta description should trip any algorithmic penalty, but if it's not in accord with the above, it's probably not optimal in the first place.
A sidenote: Duplicitous META descriptions and Duplicitous Title Tags across multiple URLs is a serious issue that could result in de-indexation. Having one URL with similar descriptions and Title Tags is not an issue, however.