Just a comment, May as mentioned many times in the Plum rain season, more so in the north such as Taipei. (One reason I stay in Kaoshuing more now is less rain on average year round). This year the rain seems to more so.

As to crowds, well that is Taiwan. But also as a side not I really dislike going to 101, as so some other tourist areas, which seem to be full group tourist from the mainland. Many of those places cater to mostly mainland tourist, and as such not real Taiwan.

As for the food, well Taiwan is known mostly for street food, or this types of foods. Its not for everyone, and often its for locals or more Asian tourists. A bit surprised though you mentioned about 101 food court and problems with language. That would be one of the more tourist geared places, I do think most vendors are used to dealing with visitors. They may not speak good English but I think enough to get by.