Old Drafting Software Won't Load

I have several programs that I used with XP but will not run on Win 7 and not nearly as old as yours. Something from 1998 is pretty hopeless. It is time to get a new program, sorry.

I found some on Ebay which were kind of cheap. I just thought I would point them out to you.
Vellum Draft software | eBay

If you have the XP install disc you may be able to set up a dual boot to run the program under native XP. Adding XP to a system already running W7 isn't that difficult. The main thing would be to have a complete image backup using something like Macrium Reflect Free to bail you out if you messed up the set up.

If you have 100GB or so at the end of C: that could be sliced off that would be plenty to run XP and a bunch of programs. You could try the program in an XP VM first as that is safer. But chances are it may run pretty slow in a software VM. Booting real XP it would run nearly as fast as before(it could be just a tad slower because it would be installed at the far end of the HD in most cases.)

If you try the dual boot scenario plan it out and make sure you can recover your current system from an image backup before risking it. But multi-boot on MBR type simple volumes is not that difficult. There are one or two gotcha's to watch out for in the main.

I have an old program "Sew Ware" that is used to transfer embroidery patterns to my wife's Singer Embroidery machine. I had to install and run it in a Win 98/ME compatibility mode. It uses RS232C interface with the Embroidery machine. I have this running in both Win 7 64 bit and Win 10 64 bit on my dual boot system.

I wonder if this one will install/run in a compatibility mode?

Also if it is 16 bit there is a chance it may run under DosBox

That would be much simpler than setting up a dual boot. Since it is often used to run Dos games it likely has low latency compared to other VM solutions.