The whole point of the first sale doctrine is that the original seller is not entitled to any special consideration once the sale completes.
So whether something was "intended to be resold" is irrelevant - you sold it to me, so I can resell it without your permission.

I also see arguments based around "copying" as being what copyright is about; it's not - distribution is what it is about.
Reselling is about transfer of ownership, not distribution. That on the technical level this transfer of ownership consists of a copy followed by a delete, should not matter - when the operation completes, there is only 1 file, so there no "copy" took place.

Once IPv6 really starts being used (granted at this rate that's years off yet, despite IPv4 having officially "run out"), with its huge range, I would not be surprised to see a push from large corporations to try and mandate that IP addresses are directly linkable to people.

Then foobar2000 (http://www.foobar2000.org/) is probably the player for you.
As a fellow media-players-should-simply-play-media-dammit curmudgeon, it ticks all the boxes. Its UI is extremely simplistic (by default - it can be customized to include things like album art etc), it has high quality playback, and a very small footprint.
It has very powerful tagging functionality (with even the possibility to script tagging operations you frequently use).
There are also many, many plugins available (to provide things like freedb-based tagging, last.fm scrobbling, ...).