Hmm I think you should be free to choose which den you want to add a spot to. If you first want to do the cheapest that is of course everyone's perogative, but personally I prefer expanding one den to the max before moving onto the next one. Perhaps a pop up saying; Your den is full, please select a den to purchase a new slot from (enter dropdown list)
Support! I just had my heart broken because the first WW in a month decided to try and come home with me... only for my den to be full because i had forgotten about a litter of four pups that had taken up the last few slots i had.