6. How long has it been around?
You want something on the leading edge, not the bleeding edge. You definitely don't want to buy a first release of anything. Let some other poor guy discover those hidden bugs. Windows Vista? Wait for the first service pack. That new line of laptops from Dell? Hang back a while. In technology, new and reliable are rarely used in the same sentence.

7.  Who else is using it?
Never buy technology in a vacuum. Get references. Do site visits. Call other users. Check newsgroups and forums. Google the vendor. Buying a new service management system? Consider going to the vendors offices for training before you buy. That way you can beat up on the instructor and talk to other users. Does the vendor host conferences or shows? Visit, ask questions, get comfortable.

8.  How will it generate profits for my company?
If a piece of technology isn't going to help you increase revenues or decrease costs then why bother? Your current system may not be pretty, but if it ain't broke why fix it? Buying software or hardware should be a quantitative decision. You should be able to mathematically calculate how much estimated profits will result, with certain assumptions, from this investment. Do the ROI and see what shakes out.

9.  Can I take a test drive?
Never buy just on a vendor demo. Get the software or hardware and test it yourself. If a software company doesn't let you drive their product, then don't buy it. If a hardware company can't give you a test piece, then reconsider. Once you make that decision and fork over the cash those eager and super-friendly salespeople will be on to the next deal and you'll be yesterday's news. Do your due diligence beforehand.

10.  Will it speak to my other systems?
Are you adding another repository of duplicate data? Are you creating additional tasks? When buying new technology make sure it's open to others. Proprietary systems are becoming more and more a thing of the past. Make sure that you can tie it to other systems. Even if there's no out of the box connection you want to still have the option of hiring someone to write the integration. Keep those options open so you don't paint yourself into a corner.

Great penny pinchers don't buy stuff just because it's neat or cool or because Microsoft tells you to buy. I have some clients that are happily using systems that are more than 15 years old! Oh it looks clunky and stupid, but the job is getting done and instead of throwing away thousands to upgrade, they're investing (or saving) somewhere else.