Double trouble?

One of two Fox stations serving Cortland County

Many small towns and even states fall between two viewing markets but mainly belong to one.  Upstate New York has a few instances of straddling the proverbial fence.  I wish to open a Planet Fitness in Cortland which is 30 miles south of Syracuse but over 40 north of Binghamton.  I'll have several TVs in the gym as they all do so I would have two of them with Fox; Fox 68 from Onondaga County back home and Fox 40 from Broome County in the Twin Tiers (logo pictured).  I'd get both on TWC and I know who to call.  As you head towards the Finger Lakes wine belt and the PA state line, two small cable companies, Southern Cayuga County Cablevision (more on that later) and Haefele have the Elmira and Rochester markets featured along with mine but only so much overlap because of retrans fees (see petition).  It'd be too far to have an antenna in these small towns.
I lived in the mid-Hudson Valley for a period between Albany and New York but it's mainly the vast flagship tri-state market but the northern part has some of the Capital Region stations too.  The cable company I had then was Freeview compared to what they have now.  I used to be able to see a syndicated show on a local station and then on a then-indie superstation right after until SyndEx caused blackouts.  Not sure if something would be blacked out on one or the other as maybe the FCC makes exceptions for double dipping areas.  New Jersey isn't too big so they're split between NYC and Philadelphias lineups.  Once Jefferson and Oneida Counties get the stations I proposed earlier, either room could be made for them on TWC, or the CNY Central ones would have to go.  The pensioners will likely tell you they grew up with just three channels and a dial!