There are also a few plugins for filament runout.
It depends on the sensor and how it is connected.
I don't know the CR-10s so maybe somebody else can anwer that for you - if not just test it
Here a list of runout sensor plugins
Not via usb printing. This feature only works when you're printing from your sd card.
I would start with a smaller print just to make sure everything is working as intended
Yeah but some octoprint features won't work that way: for example the gcode viewer, the print time left display or the layer based timelapse (if you want to create one).
You can still see the temperatures, some gcode file stats and create a timelapse with pictures every x seconds.
You're also able to control the printer.