It's because it anti-aliases to the background color, ignoring the alpha byte. A typical transparent region is filled with transparent black, so the text anti-aliases to black. If you .Clear() the region with a fully transparent version of the same color as the text you're drawing, it should look much better. For example:
region.Clear(&HFFFFFF00)
region.DrawText("My text", 0, 0, &HFFFFFFFF, font)
The same is true when drawing a bitmap to a transparent region with AlphaEnable set to True. I consider this to be a bug, and have reported it to Roku, suggesting that if the alpha byte is zero it should ignore the rest of the color for anti-aliasing, but to date they've disagreed...
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