wheel - 5:23 pm on May 21, 2010 (gmt 0)

Is there any way to acquire a site without these backlinks getting reset or discounted?

Yes.

At what point do engines realize that the domain is expired or transferred and actually devalue these links?

Don't know. Common sense would suggest time until new content is in place would be measurable. Probably also the actual content that gets replaced as being similar (though I've seen some pretty gruesome exceptions to that).

I was wondering if there is a way around this...perhaps by reaching out to the webmaster directly. Just curious!

See? Now you're thinking! There are ways, that's certainly one.