Daisy chaining monitors via a single port

Yes, this works fine as long as your monitors support multi-stream transport and you have enough bandwidth. The DisplayPort expansion card supports DisplayPort 1.4, so you should be able to drive up to 2 UHD monitors at 60Hz (or more lower resolution monitors, refresh rate dependent).

If your monitors don’t support daisy chaining, you can also get a DisplayPort MST hub, like this one - note though that the one I linked only supports DisplayPort 1.2 so you couldn’t drive two UHD monitors from it (at least not at 60Hz refresh rate).