First of all, Mark, thanks for posting that link. As I started to read this thread, I was wishing I had that map in front of me... and I was about to go search for it again. This time, I actually remembered to save a copy!
Dustin, if you didn't figure it out already, Ithaca, part of Tompkins County, is included in the Syracuse market. That's why the cable company in Ithaca carries the Syracuse stations, even though you are physically much closer to Elmira. The FCC requires cable companies to carry the stations for the market in which they are located.
Of course, there are many cases where you get extra stations from different markets. I think a lot of the irregularities with different stations being on cable can be attributed to a number of factors.
1) Heritage. In their early days, many cable companies just pulled in whatever stations they could get. This is why many systems upstate even carry Canadian stations like CKWS, and they continue to do so, even though they aren't required to. It's because people have been so used to having these stations, the cable companies keep piping 'em in. This could also be why some places get some affiliates from one market, and other affiliates from a different market.
2) Location. A cable company's service territory doesn't always line up with market boundaries. Even though it's all Time Warner for just about everyone along the Thruway from Buffalo clear to Albany, and there has been some "centralization" in their facilities... many of the lineups still follow back to the early days. If you live close to a market boundary, chances are good you'll be getting stations from both markets... so the cable company is covered as far as "must carry" rules are concerned, for customers on both sides of the market boundary.
3) Lack of Stations. The only reason WSTM gets into the Watertown market is because Watertown doesn't have an NBC affiliate. Likewise, the only reason WTVH gets into Utica is because that city doesn't have its own CBS station. I'm not sure how WSYR managed to get so far up north while WWTI was on the air, especially after the two became co-owned, but that's since been resolved. But remember, the number of viewers watching WSTM in Watertown do NOT contribute to the Syracuse market's ranking or to WSTM's ratings in the Syracuse market. Likewise for WTVH viewership in Utica.
4) Making up for market irregularities. Just as Ithaca is closer to Elmira than Syracuse... Rome is closer to Utica than Syracuse. TimeWarner in Rome carries both Utica and Syracuse. Must carry rules require TW to carry Syracuse, but they also know the Rome viewers prefer the Utica stations, since Utica does a much better job covering Rome.
Rochester basically gets squeezed because both Syracuse and Buffalo have their own affiliates for all the major networks. The only opportunity for a Rochester station to be extended out-of-market via cable would be for WROC into the Elmira area, since that market doesn't have a CBS station. I don't know if that's the case, or if cable systems in Elmira are getting CBS from elsewhere (most likely Binghamton, Syracuse or Pennsylvania).
On the good side, Rochester's stations don't have to travel as far to cover the news, so it's easier for them to get out there and cover stuff across the entire market. By contrast, Buffalo, Syracuse and Albany are similar to the NYC market (geographically) -- the markets are so expansive, many communities NEVER get mentioned unless there's a murder or a multiple-fatal crash. Something like a newly remodeled City Hall or the opening of a new shopping mall right in town will get coverage -- but the exact same event in a town 90 minutes away (but still in the market) won't get attention because... it's 90 minutes away.