Vた[時「とき」] => After having done something N5
Time
ところだった => About to… N3
Will, Decision, Doing
に[答「こた」]えて => In response to A N2
Reason, Result, Response
たことがある => Have done A before N4
Situations and Experiences
ときたら => As for person/thing A, B (surprising/negative info) N1
Considering/ Concerning
に[越「こ」]したことはない => It's better if A, it's better if it's A N1
Comparison/ Exchange
たところで => Even if A, although A (is done) N1
(Not)only , (Not) even
たことにする => To do/act/pretend as if A N1
Will, Decision, Doing
[事「こと」]ができる => Be able to A; can do A, Can A; be possible to A; N4
Causative, Passive, Volitional
といったところだ => Display an amount/level/degree A (程度) N1
Degree/ Level/Amount
としたところで、としたって => Even from the perspective of A; Even in the case of A N1
Considering/ Concerning
きり => Only A N3
Degree. Level, Amount