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I have had a great deal of success debugging and running DOS and 16bit applications in DOSBOX. You can also script nice start up scripts. So you can create a batch file, put it on the desktop, double click and it will launch DOSBOX with your application running in it. DosBox can also be configured to turn off when you exit the program inside it.
Debugging I have always used either SoftIce or TR.
Softice wont work in DosBox (im sure) but TR 2.52 has been great.
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