How do I know when it’s time to modernize or rewrite my application?
No matter how well-written your application is, you will need to refactor and clean up the technical debt over time, especially when the proper maintenance and updates have been lacking.
When your application was first envisioned, it probably had a clear set of specifications and one or two enthusiastic developers who were committed to quality.
Over time, however, they moved on and other people got involved as the specifications evolved and changed. Now you probably have a bit of a mess that may even be written in a language or platform that is no longer supported. If the language is deprecated, the code has become unstable, and developers can't develop simple features in a reasonable amount of time; it’s probably time to modernize.
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1 What is the best programming language for web development?
If there was one “best” programming language, then everything else would be obsolete. The reality is that there are so many different programming languages because there is no “best” language for any situation.
Web development can vary from a few hundred to millions of dollars depending on what is needed. You may simply need some changes to something that already exists, or you'd like to build a large or complex application.