Heres a thought that I'm sure many other people have had: Technology companies that are not dedicated to technology evaluation and adoption fall behind, and get bogged down with legacy software.
Lets say a piece of your system is horrendous, and it uses 8-10 year old technology. Lets also say that you have a new project coming up. My theory is this: If you don't evaluate new technology because it would introduce another maintenance variable into your system, then the new project will fail. Why? Because the old technology IS a maintenance variable! Even if you keep a close eye on the development of it, its still going to get out of hand. Why? Because its not good technology. When you have something difficult to do and the technology doesn't quite support it, you do a "Workaround", thinking, "Well, we'll fix that up later". Well, THERE IS NO LATER.
Most companies have there so called "valid" reasons not to do it yet. But I think for the most part none of them are valid. At the very least you need someone looking at new technologies. Yeah, its expensive, but you're not going to make significant advances in productivity without it. Is there some risk involved? Absolutely. Is the risk greater if you don't do it? My bets are on yes.
This is all similar to Innovate vs. Litigate, where a large, aging company (ie Microsoft) sues everyone in an attempt to hang on to dying technology, instead of focusing on creating new, great technology.
I prefer to call it by a slightly different name however: Innovation vs. Masturbation. I could explain, but I think you get the idea.