We tried for years to get time warner to deliver cable to our offices in a small town. They gave us installation quotes around $20k, but then when we tried to actually follow through with that, they didn't seem interested.
In the end, the holy grail was to offer them our telephone service. I don't recall exactly how we started that conversation but they examined what we were paying centurytel for a 23-line voice t1 and offered to undercut them, and since it was a new install, they ended up running fiber instead of copper. With a three year commitment to around $700/month in business phone service, they did the install (about 2000' if i recall correctly) at no charge. Once that was negotiated I said that sounded great, but could they run coax too so we could sign up for their business grade cable internet - and it wasn't a problem.
So i suppose if anyone in your subidivision runs a business, you might be able to use that as the carrot.