I bought some header/harness combos for a project and ended up with some 24 awg, IDC connectors. I looked around for an insertion tool and bought a punch-down tool which was too big. I ended up using a small screw driver, That was messy and took a long time, but it did work. I certainly like the IDC idea - smaller, cleaner, and cheaper than Molex-type crimp inserts. But I wonder if there is some tool that would make this easier.
$99? Go with a vice, it has many other uses and doesn't have to be ridiculously expensive. Just be careful to check the ribbon seating properly before clamping it down.