5. Will I be maintaining any ancient system, and what's it written in? If you don't want to inherit legacy software, go work in a startup and enjoy creating everything from scratch. Legacy software at least leaves you a work culture and a process, not to mention a frame of reference. In a startup, not only there is no much in-house software, there isn't even a division of labor.
There's legacy software... and then there are coding artifacts from another era. I'm not necessarily saying it's a deal breaker, but if your development tools consist solely of products that have been End of Lifed, you have right to be concerned how the job would affect your career development.
Poor legacy code is a liability, and legacy code that leads to suboptimal technical situations (e.g. using C++ in 2009) is a pain.