Did I break my nano?

I don't know the cause of the verification error in the first output. It gets reported here occasionally but I don't remember ever seeing a definite conclusion. I think it's usually recommended to try burning bootloader (see below).

I do know the cause of the second upload failure. When you do an "Upload Using Programmer" it overwrites the bootloader, which is required to do regular uploads via USB. So you always need to connect your ISP programmer (sounds like you're using and Uno as "Arduino as ISP" in this case) to the target board and do a Tools > Burn Bootloader before you can go back to doing a regular USB upload again. Since that's a possible solution to the first problem you'll be killing two birds with one stone hopefully.