U might not want to hear this....but if I was in your position, since your version is so very old, I would just bite the bullet and buy Turbocad Deluxe 2015/2016 and install it fresh. I am sure there are many many new features compared to the original that would make it worth your while. It would be worth your time I think to learn the new version.
You are using software that was designed 20 plus years ago for a pre W2K/XP OS, which are long gone. I think at that time, Windows 98 was in the planning stages. My guess is that your version 1 of TC was for Windows 95 or NT.
On your last question not sure on that one. Maybe one of the TC experts can help you on that one.