Comment by jm4

I don't think you're blinded by nostalgia. In the early 2000's, I worked in an organization that was migrating away from TUI to web apps. I was one of the web guys back then. We got modern, more maintainable code at the expense of usability. Those TUI interfaces are way faster.

The web failed to live up to the early promises in a lot of ways. We have complicated frameworks, complex architectures, browser headaches, etc. and what we got out of it are user interfaces that are slower than what we replaced and entire categories of bugs that didn't exist before. There's so much extra bullshit in place to overcome the fact that we are using a stateless protocol designed to deliver text documents.

The only things I would really be concerned about with your family company's app are maintainability, availability of security updates, and the use of obsolete software like XP. It sounds like you're already modernizing the code. That old OS is a disaster waiting to happen though.

I like the idea of an internal enterprise app running in the terminal on a reliable FreeBSD or Linux machine. The people who have to live in that app will be faster with a keyboard-driven workflow. A web front end is for customers and situations where you prioritize looks and accessibility over speed and usability. If you implement the the business rules in a modern middle tier and have a good database backing it, you can have the best of both - TUI for internal users and slap on a web front end for external users.