I don't like answering questions like this because he'll have to find his own 'comfort' zone. Really I'm just giving you a bump, hopefully some of the 'expert' carvers will jump in.
All I can offer is ensure you start with a heavy cake (such as pound cakes, fruit cakes etc.) to avoid the cake from crumbling or collapsing. Nothing worse than spending all that time and you end up with a bunch of cake balls. As far as 'easy start' ... again he has to go with his own comfort level. Look around in the 3D gallery and see what gets the creativity flowing.
carving the cakes frozen helps too .
Cannot believe I forgot to mention that, I just do things now without thinking about it! Don't forget that!! I fill and freeze my cakes before carving - definately. Also in between stages put the cake in the fridge to set and stay firm. And be sure you use a serated knife, sawing the cake. If he's good at templates you can create one using paper and then mark your cut lines on the cake before you start cutting.
I just realized, I need to start thinking about just what it is I'm doing more often! I just sort of do it, amazing anything works for me!
...and carve a little at a time. You can always take more off but its awfully hard to patch it back on! And keep a photo of the design right in front of you at all times. Also I find its helpful to look at somebody's cake but the most accurate way to carve is to actually work from a real photo or picture of a non cake figure. And remember that the finest details can be added later with icing or fondant, all you need is a general shape.
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