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The value of pagerank that is "transferred" to your site is divided among all the links present on the page that links to your site.
So if you want to guess at whether the PR8 link will have a big impact on your own PR, see how many links there are on that page (internal and external). If it's just a few, then you could reasonably hope to attain a PR7 after the next update. If it's a lot of links (60-70-100+) than a PR5 or maybe 6 would be a more realistic expectation.
And, I'd think it would be very bad if they tried to. Any attempt to determine if the 2 pages have the same theme will be prone to a lot of false negatives.
Yes it - in general - does not seem to play a role at the moment, but it would be an extremely interesting if not computational expensive excercise.
If Google is or would be considering surrounding text and super-imposed titles/headings of a link - both for the page with the link, as also for the page receiving the link - as important to the ranking, why not also consider it important for Pagerank?