It is possible to get Toledo TV stations in Detroit.
Now that is from the days before cable was widely available.
Maybe the local cable distributors don’t put Toledo stations on in Michigan any more, but yes, it is possible to get the signal.
It is interesting that Obama would buy Detroit. He has that demgraphic pretty well locked up and yes, the Detroit TV will reach the Toledo market either over the air or via cable.
He would be better off buying WJR radio as it targets his demo: 25-52 and is always a force in the Toledo Arbitron ratings. This would also get him the Toledo fringe which includes areas east towards Cleveland, South to at least Findlay, and west to almost the Indiana line. WJR is a 50K watt powerhouse. While known as a conservative station that is owned by Cumulus Media it carries Paul W Smith and Frank Beckman in the morning, then goes national with Rush and Hannity till 5.
If he’s buying Detroit, his internals must tell him that he is in trouble, the west side of the state is traditionally conservative and only the large union towns of Detroit, Lansing, Ann Arbor, and Flint help him carry the state.