Flo has money behind it. They money they're paying DC United and FC Cincinnati for MLS rights is definitely real. Their coverage stinks, but the money's there.
CAA deal is picking nits- whatever money Flo is sending them, the CAA is sending to CBS for a time buy on CBSSN.
That doesn't mean they really are paying anywhere close to the reported number...CBS would probably take way less for CBSSN. They go from having to pay ESPN to sublicense AAC games in 2020-21 to getting money from the CAA to put those games on their air. It cannot be overstated how little CBS appears to care about actually making any moves to expand in the marketplace with CBSSN. Channel isn't rated and that is by design. In a way, its a smart strategy, given what they'd have to pay to actually try and get eyeballs. Now there's this fog where nobody knows what the AAC or CAA does or doesn't rate on there.
As for the Hockey East thing, there is no tv, there is no plan, the entire thing is a joke. They actually have a deal with Flo, who carries the league tournament, but that's probably 5 figures.