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Just the pure satisfaction of knowing that I totally know 1001 ways to do those things more effectively and I'm going to turn this edge into cash. Simple.
Define "legacy".

What some people call "legacy", others call "reliable", "battle tested", etc.

Tech that just gets the work done and is absolutely awful in UX, UI.
Can you give me a concrete example of what you mean. A lot of things that people claim as being "legacy" are service/server level (i.e. a database engine, a runtime, a programming language, a protocol, etc) - these don't have any intrinsic UX or UI so I'm not sure I understand what type of things you're actually referring to