> Is Vala type-safe? Ie, can I exploit stack overflows in this?
Vala resembles C# most closely. It preprocesses down to C, and gives you a great API to the GObject C object system, and in particular gives you good access to glib, including its string, list, etc. libraries. It also is intended to give you reasonable access native C libraries (optimized for those that follow the GObject conventions, but not restricted to those) and has a much richer type system than C.
I'm not particularly sure there exists a language where you can say that you can't exploit stack overflows, but it's probably much harder than in your average C application and on par with C#, Objective-C, Java, Python, etc.
2. Does it support S/MIME or PGP?
3. Can I configure it to view and respond only in plaintext?
3a. When not in plaintext mode, what this guy asked: https://news.ycombinator.com/item?id=4974983