The evolution of tools

Tools that can't evolve in tandem with your process(es) and your team will eventually hold you back. Home-grown tools are a blessing in that they typically are capable of keeping up with the people who use them. They're a curse in that you can't just buy yourself an instantaneous upgrade.

But handcuffing yourself to a vendor's tool-set (and its arbitrary schedule of upgrades) is much more risky, particularly if the vendor is a big corporation. Simply because this, in essence, amounts to paying someone to know what's best for people, processes, and (to a degree) your finished product. If you're a fly-by-the-seat-of-the-pants shop and the tools encourage a more organized approach, that could be a good thing: In that case, you're purchasing methodology along with bells and whistles.

But either way, never invest in any tool-set that can't adapt with you.