Hi Amanda,
There is frequent free transportation available at all the Disney resort hotels. Among some guests, there is the perception that, in the value resort category, the Pop Century has superior transportation to the All Stars. This is because the Pop buses only stop at the Pop, while the All Star buses may stop at all three of those resorts. Among the moderate resorts, the larger the hotel, the more stops a bus will make on the grounds of that hotel. For example, the Port Orleans buses may stop at both Riverside and French Quarter, while the Caribbean Beach buses only stop at CB. However, the CB bus with make several stops within the resort, making the total time equivalent. Overall, I don't think bus service is much different at any of the moderate or value resorts.
It's very hard to guess about the availability of free dining. In the past, there have been October free dining dates, but there's no way to tell whether that will happen this year. There is a current
free dining offer happening now for dates in August and September 2012. This offer does apply to resorts at all price levels; however, the family suites and campsites are currently excluded. If you're interested in free dining, you might want to jump on the current offer rather than waiting for a later offer that may or may not materialize.
Good luck with your planning. Please let us know if you need additional assistance.