The construction of "verb1 or verb2" as in "win or lose"

When 'verb1' and 'verb2' are opposite in meaning, can you freely use the construction "verb1 or verb2" to mean "whether + subject + verb1 or verb2", if the meaning of "whether + subject" is recoverable from context?

For example, the expression 'win or lose' is listed as an "idiom" in the Merriam-Webster Dictionary:

whether one succeeds or fails

Win or lose, we'll give it our best effort.

If it's an idiom, the following should be ungrammatical:

Succeed or fail, we'll give it our best effort.

But I do find some attested examples having "succeed or fail" used in this way:

a. What else could he do? They had talked of escaping, which was against the rules, conscience told him. Also, succeed or fail, the attempt would result in his torture and death as a blood relative of the schemers. ("Essay Review of Adam Johnson's The Orphan Master's Son and Blaine Harden's Escape from Camp 14: One Man's Remarkable Journey from North Korea to Freedom in the West")

b. The master turned down his mouth and shook his head. 'Succeed or fail, he will never be finished with you. You are his, for bad or for good.' (Lord of Slaughter)

c. Sometimes, it takes more than one extra shoot to resolve the issue, but every time, succeed or fail, you learn a lot. (How Do-It-All-Yourself Shoots Can Improve Your Photography)

Granted, this type of 'succeed or fail' is not as productive as 'win or lose', but the former does seem to be in use. I know of no grammar rule where you can elide 'whether + subject' in the construction "whether + subject + verb1 or verb2", if the meaning of "whether + subject" is recoverable from context.

Is this type of elision always possible, albeit not always idiomatic, when 'verb1' and 'verb2' have opposite meanings? Or is "succeed or fail" just another less frequently used "idiom"?

Elision, or eliding, is dropping a sound, like can't in stead of cannot.

Ellipsis, or elliptical construction, is dropping a word(s).

An idiom is a peculiarity from which one cannot readily derive conventional grammar or meaning.

Personally, I think most nearly all instances of "succeed or fail" are dolled-up (idiom) versions of the fundamental "win or lose." The phrase is also an objective substitute for when you achieve a desirable outcome (succeed), but it cannot really be said that you "beat" anyone to do it (win). Also, tangentially, your examples might read just as well if they were worded "success or failure," though that is not a direct grammatical parallel.

"Win or lose" is meant to express a gamut. That is, regardless of whatever happens -- win on one end and lose on the other -- some other action will occur (e.g., "Win or lose, I am entering that competition.")

That is why you have picked up on the "opposite meaning" motif. You could just as easily apply the same elliptical construction to any appropriate set of opposites to convey the same sentiment, such as below (humorous):

Shit my pants or puke my guts, I am going to eat that whole pie. (Whether I shit my pants [one end] or I puke my guts out [the other end], I plan to eat the entire pie)

Less humorously, but still adhering to the V + V pattern you mention, we have common idioms such as:

Sink or swim, I am enrolling in the advanced calculus course.

Direct contemporary examples, adopted as a hackneyed construction, just pit some word against its own negated self:

Sick or not sick, you are going to school.

In these cases it is common to drop the repeated word, such as:

Guilty or not, I say we lock him up and throw away the key.