Expected to arrive on monday 
I'll put a plan together this weekend
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CH340 Circuit using USB-C Schematic:
USB-C Schematic bottom view:
Complete Schematic:
The difficulty will be probing the USB connector on one side and the CH340 on the opposite side at the same time. Do you have a way to hold the board in a manner to where you can probe both sides of the board at once? You need a third hand.
Is it possible to place it sideways and try to probe it that way?
Sure. However you can.
When you probe, touch your probe tip to the component lead and not the solder whenever possible
Did you have a chance to poke around with your new meter?
Haven't had a lot of free time to experiment yet but this Sunday or next week I'll pick it up a bit.
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If your problem is indeed isolated to the CH340, you can still program the defective Nano by using another Nano or Uno as an In System Programmer (ISP).
Follow the below instructions. A 10uF capacitor will be required.
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Thanks, I don't know how I didn't think about googling something similar to that.
As I said I haven't had much free time but as soon as I pick it up I'll try to troubleshoot a bit more and I'll try getting a capacitor to try that technique.
Once again thanks a lot for your help.
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