keeping a old sound card because its paid for. am i being stubborn??

philosophical driver question. my old sound card isnt supported anymore, but its paid for. i can get it working with an old driver and a few tricks. is that a reasnoable thing to do, or am i setting myself up for security issues and random crasehs?? id love to hear both sides here: ppl who kept old gear running and people who regretted it. where did you draw the line?? thx in advance!!