The Fenway Bowl is run by Fenway Sports Group (i.e. Red Sox properties including a NASCAR team, Liverpool, etc.). They care about promoting the brand and will be far more interested in having a good crowd than enriching the local Chamber of Commerce. In fact, when they announced the game the press release specifically listed geographic proximity as a key factor in selecting teams for the game.
Press Release
The Wasabi Bowl is advised by a 16 member Executive Committee which includes:
Gen DeFilippo (yes, the former BC AD who lobbied against UConn to the ACC)
CEO Boston Chamber of Commerce
President and CEO Greater Boston Convention and Visitors Bureau
Ex. Director Massachusetts Convention Center
Consultant - Marriott International
Chief Marketing Officer Boston Globe Media
So, I would think they would want at least one team that travels well and spends money in Boston and I can't see Gene D being a big booster for UConn.