Multiple Monitors on One USB C port

https://www.elgato.com/en/dock/thunderbolt-3

http://www.belkin.com/us/p/P-F4U095/

http://www.caldigit.com/thunderbolt-3-dock/thunderbolt-station-3-plus/

http://www.caldigit.com/thunderbolt-3-dock/thunderbolt-station-3/

There are many USB-C and Thunderbolt 3 docks that support multiple displays and charging though one port on the computer. Thunderbolt 3 would be better for high resolution. What resolution displays do you have, and what type of connections do they have?

it is important to understand that what you are asking for (many displays over one USB-C) is usually implemented in a dock with DisplayLink software and a display link chip in the Dock for the second and subsequent displays. These are not "real" displays, in that they have no hardware acceleration and can be slow to update.

DisplayLink software creates a software display buffer in main RAM memory and sends the data out to the external box over a slower than usual connection. Some say these displays are slow. Some users say mouse-tracking on such a display is nauseating, and others have complained that the amount of data for full-motion Video makes these displays unsuitable for that purpose.

I think full speed daisy chaining is only available for certain ThunderBolt displays, of which there are very few available.

I can't find any info on the Dell D300. Do you mean the D3000? Anyway, if it's USB, it may not be able to support two displays without using DisplayLink software, which may be slow, and doesn't work with the latest macOS.

Did you look at any of the Thunderbolt-3 Docks? They plug into a USB-C port on the MacBook Pro and should support two displays at full speed without adding software. They use Thunderbolt, so have a lot more bandwidth than USB-C, even though they use the same connector. They require a MacBook Pro, not the MacBook.

A USB-C monitor won't help. You can't connect more than one to one USB-C port.

A dock shouldn't need special software to function. Some have software to enable special functions, such as fast charging, but most ports should work with no drivers.