Yes, the critical issue is voltage drop due to resistance, which is both a function of conductor size and plug connections. One 100' #12 cord is better than two 50' #12 cords, for example, because there will be fewer contact connections.
I wouldn't hesitate to use your saw on a 100' #12 or #10 cord, assuming that you're not already at the end of a very long outlet circuit as well. You can check voltage across the plug contacts to make sure you're within about 5% of nominal (120v). As brhans pointed out in the comments, this would need to be done while the tool is under load.