We spent tons of time and effort making an awesome software program only to realize in the end the users were not computer savvy and would rather do the work in a non-technical way regardless of the benefits.

If any of the sales deal with Government entities there could be a million dumb reasons. I've seen: someone doesn't believe that there much be a catch with something so cheap--decides to buy the thing that costs tens of thousands more instead, manager decides they don't want to process paperwork for a new integration regardless of cost savings, management doesn't want something cloud based so they can "have more control over it" by buying servers, "the sales guy emails me alot, so it's kinda creeping me out", etc...,etc...

I also see alot of times the people making the decisions on technology for organizations (again, Government) are the people who don't even own computers at home and don't have even a basic fundamental understanding of the concepts of what they are dealing with. If the IT departments are brought it, it's more of a yes/no we can/cannot support whatever it is you are presenting rather than that sucks or this is smart. Actually, some of the stuff IT was suggesting boggled my mind too. It seemed like they were very against using anything internet based...