Is your main level fireplace a real masonry fireplace or a pre-fab fireplace built into a chase cavity? Is your basement finished or unfinished?

When my wife and I lived in Connecticut, we had electric heat. We saw plenty of similar home with wood burners in the basement and central heat register looking openings cut into the floor through to the basement. That enabled heat to rise through the openings to get heat to the upper levels.

My wife and I preferred to enjoy the ambience of the burning wood and more direct heat so we put our stove on the main floor. If it were me, I'd go with the insert as long as your existing fireplace is really masonry. If it's pre-fab, you can remove the existing fireplace and install a high efficiency fireplace that not only will heat the main level while looking like a fireplace, but you can also run duct work out of the side of the unit down to your basement and blow heat to that level. That what we have at our ranch house now in Illinois.

Our previous house had a woodstove in the basement that had been outfitted with a sort of big metal hood over the firebox that funneled the heat into the existing ducting system. No fan; it relied on convection, but I bet a clever person could devise a fan for a set-up like that. Adding to this was the fact that there was no insulation between the basement and the first floor living space...nice warm floors. We used the woodstove exclusively during the winter (central VA) and the house was toasty! It also kept the dirt and bugs from the logs confined to the basement.
In 2009 we built a new house but we wanted to insulate the envelope, so we opted for a woodstove in the living room. A little more dirt to contend with, but as the previous poster pointed out, watching those flames on a cold winter night is better than TV.