I get that too.I'd disagree myself. Osage (and Mitchell County) are much more north central Iowa than northeast Iowa, IMO. It's a part of the Mason City economic orbit (places to the east are not), it's flat, and it just seemed like growing up around there that everyone went to the west for sports, commerce, etc. Once you get past Highway 63 it's a completely different world geographically and culturally. I'd argue that Charles City belongs to that Mason City orbit as well, as opposed to going east.
Growing up in Mitchell County and now living in Cresco for as an adult, I definitely view Osage and Charles City as being a different part of Iowa than Cresco/Decorah/Waukon.
Just for me, Osage doesnt really belong in a conference with NK, Riceville, St Ansgar etc. And for me the radius of similar size schools always included Cresco, Osage, CC, New Hampton etc. And those not being in the same conference always seemed strange. I am not sure of all the schools that were in the original North Iowa conference, but Osage had to be an outlier to the East than the rest. I realize to the others I mentioned they are an outlier to the West, but not as much when you put CC etc in there.
To me Osage is closer to CC, NH, and Cresco, than anyone that I can think of the was in the old North Iowa conf.
But I do get what you are saying about going East from Cresco, that area does feel like a different region all together. I also can see what you mean about the Mason City region and Osage being part of that, but I also feel that at least CC is too if you look at it that way. I think Osages biggest issue is they are very much on the border between 2 regions so they dont truly fit in either but also kind of do.