No, those two not acceptably punctuated — not due to the rule books, but because they don’t pass the smell test around here. Those are way too cumbersome to attempt, no matter whether they’re right or wrong.
However, it’s obvious that if you get to elide the millions, so too the thousands.
But in any event, just because you manage to learn correct English doesn’t mean you’ll ever find anyone whom you can speak it with.
In other words, it will be awkward and stilted no matter what you do so long as you insist on conjoining so many hyphens and dashes. It’s an ungainly punctuation-heavy approach that people would never write that way, even if they might say it that way.
So either leave out some dashes or hyphens, or better yet, rephrase so that these silly is-it-ok-to-use-symbols-and-commas-and-hyphens-and-dashes-with-my-$100–300,000-words-in-one-compound-adjective issues never arise:
- a $50–60k annual funding increase
- a small business (that is, one earning $3–5m per year)