My take is that they are no more off topic than questions about Quicken... But also no more on topic than questions about Quicken.
Most such questions should be directed to the teams or communities which support the products. If there isn't any support other than SE, maybe you don't want to use that product... Though an occasional question is probably harmless.
However questions which are not about personal finance are off topic no matter what tools they are using.
I think the lemonade stand example for ledger-cli is treading on the line, not least because it is a hypothetical rather than real situation.
If the community disagrees, I will shut up. Otherwise, we may want to make our position clearer on this, and make clear that precedent does not trump policy.
(Meanwhile, I'm making that an Ignored tags and hiding ignored, so I simply don't see those questions.)