5
高【たか】 means "yield/amount/quantity" (e.g., of a crop). くくる means "to bind/tie" and, by extension, "to summarize/consolidate". Thus, the literal meaning of 高をくくる is nothing more than something like "to estimate (the capability of someone/something)" or "to assume". However, as an idiom, it has gained a derived ...
5
どうってことない
どうってことありません
どうと言うこともない
etc.
are all variations of a set phrase meaning "it's nothing" "it's no big deal". Here どう is just the usual question word and って or と the usual quoting particle. Literally the phrase means that it is not something you would ask/enquire about by saying どう.
1
条件付き means "conditional, conditionally". It comes from 条件が付く, 付き being the 連用形 of 付く and thus used as a noun/prepositive modifier. The operation is conditional.
From their FAQ:
Q: 条件付運航とはどういった運航ですか？
A: 悪天候時また台風などで海上が時化の場合、出港はするものの場合によっては引き返す可能性もあるという条件が付いた運航になります。
My translation:
Q: What kind of operation is "conditional operation"?/...
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