It's nice to see someone interested in tomatoes enough to try a second crop growing into late fall/early winter. My season begins in February and extends to frost...whenever that happens. By about this time of year I am just a bit sick of tomatoes and growing them and I am ready for so down time. Usually in November, December and January I get asked to do some gardening presentations for local civic groups, so I am never really out of the garden.
Go for all you can get between now and frost....or even later if you can cover the plants. After the first touch of frost there is generally nice enough weather to continue. I am going to begin tearing the non-producers out this week.