Yes. The line looks a size or two large for the drum of the furler. Note this is a furler on a small boat. The systems are not like a 25 or 30 footer.
To stop the furled sail from unraveling you will need to cleat or secure, perhaps cam cleats, both of the lines. With the line being large it is not captured within the sheave. It will find it's way off the drum. And this will allow the sail to unravel.
If I wanted to leave the sail and mast up on the boat overnight, I would get some velcro ties to wrap around the sail in a couple of places. This would help to keep the sail wrapped. You can also sew a sail sleeve to wrap around the sail like a jacket. That would also help protect part of the sail from the sun and weather.
If like most 14ft boats, I would pull the mast and store the sails in a covers area out of the sun when not in use. This has the added benefit of teaching young sailors the work of rigging a boat. A good skill for them to have.
The second picture looks like a "fast Drain" to empty the boat of splash and rain water beneath the hull. As you go zipping around you can flip the drain open and water will be sucked out of the boat. Not to be used sitting at the dock. Water might start filling the boat. We used them on Flying Dutchman when out in the ocean on a strong breeze. Took seconds to empty the wave splash coming in over the bow.