This is potentially problematic in a few ways.
- The monitor may not be a pure USB device, it may be using an alternate mode like displayport. This cannot be supported over an A connector. Depending on the device this may result in either reduced performance or no video at all.
- Even if the monitor is a USB device, USB C is a reversable connector. Responsibility for handling reversal falls on the device with the USB C socket. So if your monitor is a USB device and has a USB C Socket you are ok, but if the monitor has a USB C plug there may be issues.
- Volt drop and signal integrity may become an issue, but if the cables are short this is unlikely to be an issue.
- A cable with a USB A plug and a USB C plug will be coded with the USB C end as "downstream". If your bulkhead adapter has two A sockets (rather than the A socket on one side and B socket on the other that it should have) then you will likely have to use a C plug to A socket adapter in combination with an A plug to A plug adapter to make it work.
USB C couplers may also be problematic. The USB C standard was not designed to accomodate them, and they may either only work one way round or not work at all depending on the design of the devices and the coupler.
IMO if you need to pass your signals through bulkheads or similar, USB C is probablly not the right technology for the job.