Some years ago, I took on the support of a WebForms app for a vehicle hire company. The app was used by a team of about 30, and it was a small-scale deployment—they had one server hosting the database and one server running the web app. Although small, it was the core application for the business, and everything they did ran from this app.
The app had a very simple architecture: just one web application and an SQL Server database. Initially, I did a lot of work to improve the performance and quality of the application. After that, it became a caretaker role, where I would manage two or three releases a year, adding new features or fixing old bugs.
These releases were always more difficult and time-consuming ...