I'll be very interested to hear the feedback, as I am in a similar boat. I currently have a Dinolite Pro USB that is about 10 years old, so I can give you some feedback about the dinolite pro.
As you mentioned, I really like having the direct connection to the computer for immediate viewing and easy upload. Sometimes I can get good pictures with it, however, I have a very difficult time with setting up the dinolite and getting good lighting. On real close up pictures, I often have parts of the coin out of focus.
Here are some pics. I've actually bought a couple of USB LED lights that I have attached to the stand such that they move with the microscope, with the thought that I can get lighting at 10 and 2 and it is all one unit and easily portable.
Can someone please tell me why these are rotated. I have rotated them on the computer and saved them, and they still turn out sideways when I upload them.
I personally have a hard time getting the magnification, focus, and coin location just right. The microscope stand has both a coarse and a fine Z (up/down) position setting. Therefore, you need to manually position the mechanism on the vertical stand, and then you can fine tune the vertical position with a turn wheel that moves the microscope about two inches. I am not good at this process, and find it very time consuming, as I often have to move the slide mechanism multiple times to get it right.

As I look for a better setup, I am looking to have a full Z (vertical) position setting for the microscope (or camera), as well as having an XY stage for the coin to sit on. However, this doesn't really address the issue with lighting and parts of the coin being out of focus.
Unfortunately, unlike you, I am uneducated about photography, and all the terms about macro lens, f-stops, apertures, white balance, etc are confusing. Ideally, I would have a point and shoot type setup.