I don't see why Uncanny X-Men #444 should be recommended more than any other issue. It's set in an era of Uncanny X-Men's story-telling that is widely forgotten. It was the return of Chris Claremont & Alan Davis, but otherwise it still featured a roster & events that are pretty unspecial when compared to the rest of the X-Men's history.
The problem with Uncanny X-Men is that it's an ongoing soap opera. There are few outstanding moments to recommend new readers to jump in. Especially as the drama is drawn out over years, and there are so many decades to look back upon. That's why Marvel recently created the .1 issues. Therefore a good catch up issue for the Uncanny X-Men would be #534.1. That'll help you understand the set up for the X-Men in recent years & now.
However, if you really want to check out events from the past, then your best bet isn't to buy individual issues. It's to hit the internet.
Search Amazon or eBay. Amazon will give you trade collections; you get the whole story in one condensed package that sits neatly on your bookshelf. eBay will give you 'lots', 'sets' and 'collections'; Search for 'X-Men' & then make sure you hit the link down the left-hand side that says "Collections & Lots"... et voila! You'll find that there is a lot to confuse you, but as long as you take the time to investigate each lot individually, you'll discover whether they are consecutive runs (sometimes they're just random, hotch-potch issues), and you can sometimes get a few years worth of stories in one go.
Don't be afraid of starting points or specific issues. Everyone gets into TV shows all the time without having watched the first episode. So just dive in there!
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