If you're familiar with Reddit, you'll know how all of their posts containing pictures get a small thumbnail preview beside the title of the submission. How does Reddit go about doing that? Does it just check to see if the link ends with .jpg, .png, .bmp, etc?
reddit will try to pull a thumbnail from any source--not just an image URL. This is done firstly by having set rules for specific sites, and secondly by having one generic process for retrieving thumbnails for unknown URLs--and is an automated periodic task.
One of the (many) benefits of reddit is that the source code is open, and if you understand Python, you should check out /r2/lib/scraper.py for a more detailed view at how this process works.
Also, while StackOverflow is a great place to have programming-related questions answered, you might also want to check out reddit's own /r/redditdev for information on reddit development.

If you have to resort to the last option, one technique I'd recommend is to extract multiple images, and A/B test them to find the one which has the best click-through rate. That way you can nearly always get the best one.
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