A couple more ideas from someone who messes around in a wood shop a good bit:
Definitely want the press and a padded clamp.Carefully set depth limit on the drill to match insert.
Sometimes on irregular shapes, it also helps to support the ends of the work piece, I have two bags of birdshot I use to wedge around and under things beyond the clamp jaws. Bean bags or a sack of dry beans etc would work too in a pinch. These take on the shape of the work piece and help resist movement. Sometimes things are hard to stabilize, sometimes they aren't, this trick helps me with odd shapes.
I sometimes use lubricant like Kennym said to prevent glue sticking (vaseline or paste wax). As he said, if you get the lube anywhere the glue won't stick.
As an alternative, consider neatly putting some painters tape over the area before you drill, and drill right through the tape. Put it on real smooth with no wrinkles. It will help protect the surrounding finish, and will mask the area for gluing the insert. It also gives you a markable surface to easily lay out your drilling spot beforehand.
Carefully pull the tape after you put in the insert to remove any excess glue.