A question word + かというと can literally be read as "if I were to tell you who/what/when/etc." Its intent is to emphasize the information that follows, or to purposefully delay providing that information to create suspense or dramatic effect.
どちらかというと is a set phrase that means "if anything" or "if I have to decide." A "why" word like どうして or なぜ + かというと is used to mean "because" or "the reason is." Other question words with this phrase can be read as "to tell you who/what/when..."
スミスさんは、日本語が上手だ。なぜかというと、日本に長く住んでいたからだ。
Smith-san's Japanese is good. The reason is that he lived in Japan for a long time.
私は辛い食べ物が好きだから、どちらかというと日本料理より、韓国料理の方が好きだ。
I like spicy foods, so if I had to decide, I like Korean food more than Japanese food.
A: 今度のミーティングはいつですか。
B: えっと、今度のミーティングはいつかというと、あっ、来週の水曜日ですね。
A: When is the next meeting?
B: Er, to tell you when the next meeting is, ah, it's next Wednesday.
このコンピュータのメモリは、どのぐらいかというと、2GBぐらいです。
As for this computer's memory, to tell you how much it has, it's about 2 GB.
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