I see it like this:
The Rama says that it’s lichatchilah mutar to collect on a debt with wine. Dealing in Stam Yayin is assur lichatchilah.
IMO, the Rabbinic issur was only for dealing because dealing leads to all the problems. A one time sale, re-gifting, or collection of a loan is OK because those infrequent activities don’t lead to all the problems.
It seems to me that you are saying that for a real hefsed it’s lichatchila assur, then for a little hefsed all the more so.
If my above assertions are correct, I’m looking at ‘why’ and you are looking at ‘what’.