Is it possible to do this

Hi,

No, not by default. That would require the development of a module for the left sidebar display for the progress of the configuration and of a plugin to redirect to the next listing of products after one is selected and to ensure that everthing has been properly selected when reaching the checkout.
A simpler solution would be to have everything on one page. With custom item fields and a plugin to calculate the cost based on what has been selected in them it should be possible.
One simpler alternative would be using Calc builder which integrates with HikaShop:
www.moonsoft.es/joomla/product/27-cb-price-calculator
That way, you could build the interface to enter the information and calculate the cost with Calc Builder which would then redirect to the HikaShop checkout for the user address, shipping and payment. I think this would be your best bet so I would recommend you checking with the developer of Calc Builder on the details of your project so that they can tell you if it's all possible with it plus HikaShop.