The problem I find with Media Monkey is the gaps between the tracks - I agree that in many ways it is superior to Windows Media Player, both in terms of sound and ease of use (especially to WMP 11, whose operation seems deeply counter-intuitive to me) but for long works subdivided into tracks, WMP has the edge)
Playback
How do I enable crossfading and gapless playback?
You can set crossfading and gapless playback settings via the included DirectSound output plug-in:
Go to Tools | Options | Output plug-ins and set DirectSound as the output plug-in if it isn't already.
Click the 'Configure' button to configure the plugin.
To enable Crossfading, select the 'Fading' tab
Change the default fade length to 600ms (or longer)
Double-click 'On start' and then 'On end of song' to enable fading
Click 'Apply' and then 'OK'
To enable gapless playback:Select the 'Buffering' tab
Increase the 'Buffer length' to 5000ms
Increase 'Buffer-ahead on track change' to 3000ms
Select the 'Fading' tab
Ensure that fading is disabled for 'on start', 'on first start', and 'on end of song' since if fading is active, gapless playback will be disabled.
Select the 'Other' tab
Check "Remove silence..."
Click 'Apply' and then 'OK'
no gaps at all now!