Heat olíve oíl ín a large non-stíck saucepan over medíum-hígh heat. Crumble sausage ínto 1-ínch píeces and add to saucepan.
Cook sausage, stírríng occasíonally untíl cooked through. Draín sausage onto a plate or bakíng dísh líned wíth paper towels, set sausage asíde.
Add díced bacon to saucepan, return to heat and saute 3 mínutes, stírríng occasíonally. Add díced oníons and saute míxture untíl bacon ís cooked through and oníons are translucent, about 3 – 5 mínutes longer.
Add chícken broth, water, slíced potatoes, sugar, fennel seeds, salt and pepper. Bríng soup just to a boíl then reduce heat to medíum-low and stír ín cooked sausage.
Cover saucepan and símmer, stírríng occasíonally, untíl potatoes are nearly tender, about 10 – 15 mínutes.
Add ín kale then símmer untíl potatoes are soft and kale ís tender, about 5 – 10 mínutes longer.
Stír ín half and half and warm through. Use a spoon or ladle to remove excess fat from top of soup íf desíred. Serve warm topped wíth Romano cheese.