I currently have two setups, a popsicle and a shaped board. In the past, I've switched up to shaped decks in the winter to have fun and get through depressing winter months of skating once or twice a week at indoor parks, then back to popsicle when it warms up and I'm back to skating a lot of street.
However, I'm really happy I have the option to choose either setup right now, and I'm going to do my best to always have that option from here on out. If you are fortunate enough to enjoy the best of both worlds, do it.
That being said, I think I could skate the Polar Dane 1 shaped board forever without missing Popsicles too much. I can do everything I want to do on ledges and flatground with it, and transition (which is my personal favorite) feels so sick on that board.