I am sometimes guilty of overthinking things. Being a Software-type, I am over-analytical in just about everything I do. I weigh options, I seek advice, and usually I make my decision (after a while). Whenever i see people looking to invest in software, I see a similar situation. Now, being careful and analytical is very important, especially in a major investment like software, but more often than not, there are a few elements that get in the way of a good software selection process. I thought I would throw out a few easy things to remember when entering into the software selection process. This is a simplified list, but it does give a certain perspective to the whole endeavor.