Iirc, for the boots you need to help Pap the shopkeeper. See the notice near the entrance, and look for the fungus down in the dungeons.

The Oracle you don't need. She's there to help you acquire character flaws -- those are sometimes taken by experienced players for challenge.

Yes, as an assassin you'll learn a new kick once the last one is at 91%. It is a good idea to get them up as early as possible.

For leveling areas, try "help newbie3".
Also, see the wiki on Dioxide's (qhcf.net). There's a world map, gear and ranking area lists, among other useful info.