Hi,
You should create Debug log like described at https://www.mediamonkey.com/forum/viewtopic.php?f=13&t=69 with MM5, also you could be useful to leave MM5 for some period of time to see if Auto freeze debug trap kicks in and MM5 throw some error dialogs?

In Addition to above you could try to do a clean install in another portable folder like c:\MediaMonkey 5 2104\ and see if you can confirm behavior.

Since I enabled auto organise, on startup, I have a spinning circle top right and hovering mouse it shows me file names.

Randomly, after a period of time the Monitoring xxx of xxx stops and does not increase in number - the circle continues to spin.

Only way out of this, eventually, is to kill the MM processeses with task manager.

Using 2104 build.