So what do I want from my software?
Furthermore, Easy things should be easy, hard things can be hard. (Mathematica and its book by Wolfram are a great example on making simple things simple, and difficult things possible.)
I like to use any tool that helps me to get my work done. But I shy away from tools that seem to make it difficult to switch to a superior tool if it becomes available. Similarly, I shy away from tools that do not collaborate well with other tools I use. For example, a LATEX editor that does not allow me access to the standard underlying LATEX ASCII text violates both criteria.
Furthermore, I like software tools that are widely used since they tend to be reliable (so called pseudo-standards) and ease the exchange of information and data. ( The masses are great at avoiding bad software. But don't expect silver bullets in mass software. ) Furthermore, new competing software will probably attempt to smoothen the transition for users of standard alternatives.
Example for good standard software solutions to common tasks are LATEX for text typesetting, GNU make makefile implementations, or RCS for version control. Only if the software directly relates to my research area might I forego standard software for potential silver bullets.