Taking this sentence as an example:


I always have a hard time knowing how to read 如何; いか, いかが, even どう or いかん sometimes..

I've checked if the question was answered previously, I hope I didn't missed it!


In the sentence you gave it is functioning as a noun, so its reading is [如何]{いかん}.


Source: デジタル大辞泉

Recognizing from context the part of speech 如何 is functioning as (noun, adverb, adjectival verb) is helpful as a first step. Also, recognizing if it is part of a set phrase e.g. [如何]{どう}あっても, [如何]{どう}致しまして, [如何]{いかが}なものか, [如何]{いかん}せん, [如何]{いか}に should get you there in most cases.

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