There's no problem splitting an OUTPUT by tying two wires in parallel. But, I wouldn't split an INPUT that way.
I know some SB16s have separate line and speaker level outputs. That would be ideal. Assuming your speakers are powered, they just need a line level signal and should be used from the line out. Headphones will work from a speaker level output, just be careful with the volume. You might need to build in some attenuation. A series resistor should do OK in this application. Appropriate value might be 47R, plus or minus one order of magnitude. (Depends on your headphone impedance and the voltage being output by the sound card.)
Having a back panel mic AND a front panel mic plugged in could be problematic. Not such a big deal if you just use the front panel jack exclusively, regardless of whether you're using a desktop mic or headset mic, for example. Or whatever it is you kids do with PC microphones.
The *correct* way to do all of this is to tie in to the circuit before the output jack with a switched jack. When you plug in to the front panel, the jack opens a switch which interrupts the signal going to the back panel jack. With nothing plugged in, the front panel jack just loops the signal back to the card and out the back panel jack. You might be able to do this with the output, if your card has a shared line / spk output jack with jumpers to determine whether to amplify the output or not. No idea if any of the SB16s had a mic jumper on the board, nor what its purpose would be if it did exist.