Why is this in Emulation?

Whoops, looks like I ended up creating the thread in the wrong place after I logged back in, sorry.

TMIDI: Tom's MIDI Player

Unfortunately that player doesn't seem to have Playlist support and only supports infinite looping (as opposed to "X amount of times before continuing").

Moved, uh, to Marvin. (or should it be Milliways?)

Get this (don't let the name fool you , the karaoke stuff can be turned off completely) -> http://www.vanbasco.com/karaokeplayer/

keropi: Someone else just mentioned that one, unfortunately it doesn't have loop-point support (it can either loop the entire track forever or nothing) so it isn't of any use, otherwise it ticks all the boxes.

I thought there was some sort of free version of Cakewalk released at some point. In any case, they do have demos at the moment which are fully functional aside from being unable to save. Not sure if they have playlist functionality, though.
https://www.cakewalk.com/Products/SONAR/Try-SONAR

I've tried Sonar, it doesn't support playlisting at all (as it's designed as an editor/DAW, not a player) and it seems to ignore MIDI loop-points on playback, you have to manually set loop-points separately for some unknown reason. So CakeWalk's definitely out.

Enverex wrote:

WinAMP should fulfill the criteria but unfortunately I've found that it sticks notes when looping tracks rendering it a bit useless (e.g. when it hits the loop-point it will loop, but one of the instruments will get stuck on).

I often used winamp with the setting "GM reset" between tracks. But I don't know if that works with the looping you want to do.

Unfortunately not, I did have that set but it only fires between tracks (I'd imagine it would just break instruments anyway if it did fire at the loop points).