Haven't posted in this thread in awhile but I figured I'd let you guys know that I did not disappear and abandon the Whiplash project. Well, I abandoned the idea of re-writing the game with my own engine but it is because I started getting really good at using Ida and now I feel quite confident in being able to do the better thing that I wanted to do originally anyway which is properly decompile the entire game and implement all of its functionality faithfully in a way that builds and runs on modern machines. Where necessary, DOS-specific functions are substituted with SDL and Windows/Unix equivalents but otherwise it is original Whiplash code. I've been making huge progress lately and have most of the functions regarding loading assets and configuration done, sound and music playing, and a software rendering pipeline to an SDL window. This week I got into the main menu and have fonts rendering.
https://github.com/Zizin13/Roller

I can now get into the main menu and render fonts

Perfect timing. I can now get into to main menu and render text.