Hi,
It is not a silly question at all.
You don't need the reset pin for debugging purposes per se. It is more about how the debugger can get control over the target, and using the reset pin is one way to get the hardware in a known state. But the debugger still can use the data/clock JTAG pins to talk to the hardware. But that might not be possible if the device is in a low power mode with say the debug block disabled to safe power. In that case the reset pin is a way to get the device back to life and to a known state.
What I do in my designs where I'm using the reset pin for other functions (say using it as a GPIO pin) is to keep the reset functionality present for some time (say 500-1000 ms) after power-on. That way I have a window right after power-on in which the debugger still can use the reset pin to get control over a target. Still having that reset functionality available can be critical for some applications.
I hope this helps,
Erich
PS: you might find more information on this topic here: Using the Reset Button on the Freedom Board as User Button | MCU on Eclipse