Dashes with other punctuation

So, I'm wondering if the following examples would be permissible? With regards to the punctuation, I mean; in terms of content, they're deplorably lame, but they're just examples to illustrate the punctuation issues! Also, I can't make an en-dash in here, so I've put two hyphens in to represent an en-dash (in preference to an em-dash).

1) He chose the challenge -- the adventure, and he would live to regret it.

Is this permissible or must there be an closing dash with no comma.

2) He chose the challenge -- the adventure; he would live to regret it.

Is that permissible? It would surely be if a full stop were chosen instead of a semicolon.

Additional question: If you choose to use an em-dash, may one still have spaces at either side or is there some strict rule forbidding it? I know it is probably common not to have the spaces, which is one of the reasons I prefer to use the option with the en-dash.

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