1

The official JLPT N1 sample contains this sentence:

いまさら後悔してみたところで、してしまったことは取り返しがつかない。

Which I would translate as:

Even if it is too late I tried to feel sorry, but what has been done can be undone.

If my translation correct, I fail to see any situation where anyone would say this, especially the "tried to feel sorry" part. The sample does not give any context unfortunately. Can you imagine any scenario where someone sane would actually say this?

2

This 〜たところで... can be used in a positive way, but is usually used to express the opinion that even if a condition is fulfilled, it's pointless/meaningless.

"Even if (I) came to regret it, it'd be pointless [too late], what (I)'ve done can't be undone."

I think this is a different usage of 〜てみた: "二 -> ① -> ㋑" at Daijirin which connects to a non-volitional verb, indicating the completed action creates a new state/awareness.

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