I have run the Taulbot Pace Calculator software on the Windows 7 and Windows 10 64 bit operating systems. I think the problems occurs when installing off the original cd's. I originally installed it on a Windows XP 32 bit system. Instead of reinstalling off the original cd, I just zipped the the whole folder with the program in and moved it to my new computer. Unzipped it and made a short cut for it to the desktop. You don't need to zip it up, you can just move the folder.
As far as the Help file, I found this link on answers.microsoft.com. About the 7th reply down is a reply by Alan Copp, that has instructions and links on how to get the Help file to work on Windows 10. It's been a while since I did it , but it worked for me on both Windows 7 and Windows 10 64 bit systems.
I would think American Turf Monthly could repackage this program and get it to work. Hope this helps.
Help File Info