Hi Dan,
I will try to answer your questions best I can.
I cut a lot of vinyl on my CNC using a drag knife with 0.5mm tip offset - the corner rounding has never been a problem.
LazyCam - top left click on 'File' where you will see that you can open HPGL and PLT files. Once they have been converted to GCode you can feed them direct to Mach3 for output to your machine or save them as a GCode file.
Target2GCode is available on the 'Majosoft' website (you will have to search for it)
http://majosoft.com/ but it sounds like it is the VB runtime components that you are missing and these can be obtained from the Microsoft website
http://support.microsoft.com/kb/290887Tweakie.