It seems that regardless of how old and practiced you get at something, sometimes you just need your mother to make it come out right.
I went to my parents' house to bake the chocolate chip cookie cake again. . They also have a kitchen scale and since ingredients are given mostly in weight measurements with a cup measure as a secondary, I was able to measure more precisely.
I don't know if it was one of those things that was the difference between yesterday and today, or if I left something out accidentally yesterday, but the cakes today came out perfectly. The batter was much wetter and more smooth and spread while baking like it was supposed to. The result was cookies that looked like cakes rather than cookies that looked really big and are hard to cut. With the remainder of the icing that finally set enough over night, the cake came together perfectly.
So, in the end, the chocolate chip cookie cake came out spectacularly.
I offer big thanks to my mother and her kitchen.
Now, what to do with the enormous hard cookies that are in pieces all over my counter top - I guess the coworkers are getting an extra treat tomorrow!
As for the road trip. Vermont is being skipped at the moment because it is the only Passover-friendly recipe in the book, so I figure I might as well wait it out. And the Boston Creme Pie will be done in May for my grandmother's birthday, since BCP is her favorite.
Next stop: Connecticut Hartford Election Cake (Nutmeg spice cupcakes)