Comment by sasjaws
I'm building a reader app that tries to solve this exact problem by providing a range of gradually simplified versions of each article to match your proficiency. So you can stay in the sweet spot, or work your way up version by version.
If your target language happens to be Chinese then you can give it a try at https://reader.longyan.io/landing
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Sure. This kind of project seems to be pretty common. I'd strongly suggest using traditional characters as a base because it's very easy to map multiple characters into simplified forms but much harder to disambiguate simplified forms into the traditional versions.
Related comment on another app: https://news.ycombinator.com/item?id=43769831