It depends.
-whether my PSU can deal with another GPU (crossfire/SLI is typically more demanding than a more modern single card)
-whether or not I can get a decent price for my current GPU.
-whether I happen to spot any good prices for either the single card, or the one that I would use in combination with the old card
One thing to take into account is that typically, you can find your old card secondhand for almost nothing (*if it has been out for a couple of years or more). This can make SLI/crossfire really tempting.
For me, on the one hand I love the simplicity of using a modern card. This tends to be quieter, not run as hot, does not draw as much power and so on. On the other hand I love using old and "discarded" components and use them.
A little bit of topic, but I recently did something that really showed me how much you can do with the hardware that people sell for almost nothing when it is one or two generations old.
My nephew wanted a good gaming PC but was worried he could not afford it. He literally had almost no budget. I took an old case, bought 2x secondhand GTX 560Ti for almost nothing, bought a i5 760 with mobo for almost nothing, bought some new RAM, a new PSU and used the HDD from an old work PC. We spent less than 250 euros total, and he can play anything, like Skyrim, The Witcher 2, BF4. You should have seen the little dude and how happy he was. He thought he needed to save for at least another 2 years. I bought him a new monitor to go with his rig.