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SleepyHead will not start
#11
If you google "BrokenGL or OpenGL? - TNET Sleep Informational Site" there's a page where Mark talks about the QT graphics library being glitchy on older operating systems and sometimes crashing. It might be some kind of gruesome QT/graphics drivers issue. There seem to be a bunch of youtube videos about fixing a Minecraft - Windows 7 - Open GL issue.
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#12
Another thing to consider: If you have both the 32 and 64 bit versions installed, it may be loading the wrong DLLs sometimes. Uninstall both, then install just the 64-bit (assuming you're running 64 bit windows, contrawise if you're running 32-bit windows).

Since you're a programmer, if you feel like digging in and looking at what thread is hanging, you could try using process explorer or one of the other sysinternals tools. They will also show you what DLLs are loading, etc. ProcMon is OK for basic info, but if you want to dig in, try these tools

(I can't post a link yet, but just add https:// in front of it)

technet.microsoft.com/en-us/sysinternals/bb795533.aspx
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#13
I also have had problems with SleepyHead not running at times. When first installed it worked fine for many times over several weeks but then one day would no longer open. Had this problem with the 32 bit version and then again on the latest 64 bit version.

Found that if I delete the SleepyHead Files folder, the program will load and run fine, one time. Traced the problem to the Preferences.xml file which the program writes to each time it closes. I have two identical computers; SH has no problems on the second one and runs and exits with no problem, but not on the first one. I cannot find anything strange with the first computer.

My final solution for this strange problem was to copy the Preferences.xml file from the computer that works fine and place it on the my "troublesome" computer as a read only file. Everything works fine now. This is really strange!

So, if you have a problem similar to mine - try replacing the Preferences.xml with an empty, read only file

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