We'll start with the easy question about the saw kerf. You can select between a 1/8" or thin kerf blade by clicking File > Options. Any finer delineation would be not apparent.
with regards to starting at the end and working backwards, this isn't really possible because the software doesn't know what backwards is. For example, if you started with a 3rd generation design, for example, what happened with the first two generations? There are so many possibilities, the software wouldn't know how to proceed.
instead, you should start by creating a pleasing design with little regard to final dimensions. Once you have a desired design, it is a simple process to adjust sizes by simply changing the width of the first cut as that along with the angles chosen will determine the final width of the repeating unit.
i use Lamination PRO all the time to make vertical grain cutting boards and here is my method. I start by making a boar with approximately 11 strips of three or four species. Lampro has a number of species in vertical grain and you can add as many of your own as you wish. Once you display the laminated board, change the angle of the first cut to zero and click the Flop button and change the width of cut to something like 1". This will show you what the complete board will look like and you will see where the joints will be problematic. You then just need to go back to the Laminate Wizard and change widths of the strips until the finished cutting board has the look you like.
when you download and install the trial, it will install samples into a folder named My Lamination PRO > Samples and you'll find a sample cutting board there.
please let me know if you have additional questions.
Lloyd