Until recently I helped running an old Clipper/dBase TUI application from the late 80s for a family member. We managed to run it successfully until they retired. vDos (vdos.info) was a huge life saver for this application. It's similar to DOSBox, but more tailored to business applications. The big issue was always to find compatible printers for the old application, vDOS includes some emulation to print to any Window…
What type of business was it? What kind of functionality did this TUI application provide?
Over time it even got extended to interface with a few external systems, mostly by reading and writing text files to specific locations.
It was deployed on one location with 2-5 concurrent users on the same database. The workflow was something like this: open customer/new customer, read/add notes, register products/services provided, print invoice for customer, print monthly invoice for insurance companies including all the required information (hundreds of pages).