I'm probably no help....I just guess as to servings and try to be somewhat generous. If they ask for 25 servings, I bake enough for 30-40 (depending on what cake pan I'm using, just round up a good amount).
As to cutting guides...haha...I figure if they want a weird shaped cake, they can figure out how to cut it! 
No really...haha....if I do have boards and supports inside I'll explain where they are and how to cut it in layers, but for the most part, if they don't ask, I just let them figure it out. There's really no easy way to cut and serve a crazy shaped 3D cake.
As to cutting guides...haha...I figure if they want a weird shaped cake, they can figure out how to cut it! :twisted
I luv it! You are a classic!
Haha....I have had customers ask how to cut a cake (like a 3D dog or some other odd thing) and I will laugh and just say "Hey, that's your problem...I just MAKE them!" Of course I smile and assure them I'm just giving them a hard time and I at least try to explain how to cut it. Sort of. Some of them are hard. Like...pretend its an animal cracker and bite off the head? *shrugs*
I made the molded pan 3-D duck cake once for a friend. She asked how to cut it. I said, "I'd whack the head off, then split it right down the middle, then cut each half in slices." She said at the shower they were actually fighting over who got to whack the head off of the duck!
Hi, 95% of the cakes I make are sculptured. What you need to do is work out how many slices you would get from the cake tin before you shape it and work out what percentage of it you have removed. I you shape it and put it back on to the cake, then you need to allow for this also.
I hope this makes sense but you would be surprised how many people these types of cakes do feed.
Good luck,
I've wondered too & I think my biggest dilema would be how much to start off with. but I do like your tip Makeitmemorable
I made the molded pan 3-D duck cake once for a friend. She asked how to cut it. I said, "I'd whack the head off, then split it right down the middle, then cut each half in slices." She said at the shower they were actually fighting over who got to whack the head off of the duck!
I do the lamb cake every Easter. The head and butt are the first things to go. 
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