I continue using legacy equipment as long as it's working fine and hasn't caused me too many problems in the past. If there is no reason to get rid of a perfectly fine piece of hardware, don't.
- What factors do you consider when trying to determine the risks associated with continuing to use the equipment?
The top factors I always consider are security, scalability, and reliability. Does this piece of hardware meet security standards? Will it be able to handle more load when upgrading the network infrastructure in the future? How reliable has it been for me in the past?
Do you need the support that was offered prior to the hardware's end-of-life period? If so, you can look into other companies offering support for outdated hardware. If not, save the company some money and let your boss know you can handle the equipment without further support.
- If you believe that the risk is to great, how do you convince management to loosen up on the purse strings in a difficult economy?
This is a tough task to accomplish, it requires a fair bit of social engineering on your part. But whatever you do, don't lie. Be up front with your boss and learn to tone down technical jargon into information he or she can understand.
As opposed to saying something like this: "We need to upgrade the backbone on our network as it will not be able to keep up with the required throughput with the addition of a new office full of employees".
Try something like: "We will need to spend roughly $1000 on part X. Adding a new office means we will need to upgrade our current hardware to handle more computers."