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Don't worry about having two lines per frame. VSfilter is actually faster at rendering two small lines than one big one. For drawing the overlay masks, I recommend you to look into assdraw2 (it's available somewhere on the Aegisub forums). Aegisub will eventually support drawing \p vectors in much the same way as it supports the vectorial \clip now.
If all you want to do simple stuff like what's shown on your screenshot, doing it with ASS feasible and shouldn't be too slow. Otherwise, it might start becoming a problem. However, I don't recommend hardsubbing over the original japanese text, as viewers who actually speak some japanese will be bothered by it.
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