First off, thank you for maintaining html2text, it's great!
Right now, list items are always indented two spaces per enclosing list. This is generally right, but doesn't work for <ul>s nested inside <ol>s. Those need three spaces (at least) instead. Details here in the Common Mark spec.
I have a PR ready for this, I'll submit it in a minute.
For example, this HTML:
<ol>
<li>ordered</li>
<ul>
<li>unordered</li>
</ul>
</ol>
needs to convert to this, with five spaces before * unordered instead of four:
1. ordered
* unordered
3. end
Tested against HEAD with multiple Python 3 versions.