Thought I was getting the hang of this, now I'm completely lost

Look at the hair immediately around Liberty's face. Parts of this area will appear slightly flattened and be a duller gray than the surrounding area, rather than the bright shine of an unworn coin. Also, look at the stars. There are lighter areas around them, which suggests that they protected those areas from the wear that the rest of the fields of the coin endured. If you move the coin around in a lighted area, you should be able to see more luster around the stars and rims of the coin than you do in the middle of the fields. I have a coin which shows a contrast between the area protected by the legend and the unprotected fields very well. I will see if I can find it for you.

 

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Found it! Do you see the orange-ish periphery around the devices? Those areas were kept from wearing by the devices which stuck out of the coin. Basically, the stuff that is coming out of the coin acts like a shield for the fields immediately surrounding them. This is an XF coin, but the areas around the legend "United States of America" and "Colombian Half Dollar" still retain mint luster because of this effect.

 

I thought the coin in question is very similar to this one (NGC MS62):

http://www.ebay.com/itm/1880-O-Morg...81?pt=Coins_US_Individual&hash=item3a88d45e8d

The breast feathers on the eagle even look more defined than the one on eBay.

This one also seems to have more obverse wear on the top of the hairline:

http://www.ebay.com/itm/1880-O-MORG...24?pt=Coins_US_Individual&hash=item35cc9b4b5c

If anyone can explain the difference to me as well, I'd appreciate it.

 

The problem is, these coins were all photographed at different times in different conditions. I agree that the second coin looks like it is worn on the obverse, but it can be very hard to tell from pictures sometimes. The first one has visibly more luster than the OP's coin. As for the breast feathers, they are unimportant in this case. On an unworn coin, the breast feathers level of detail is determined by the quality of strike, and strike isn't extremely important until about MS65. Anything above MS60 should have no wear according to technical grading, but market grading dictates that really nice AUs can get a low MS grade. That may be the case for the second coin you posted.

 

One thing that is making it much more difficult for you to understand grading is that you have a coin that has been dipped. It might have been dipped because the owner preferred white coins or it might have been dipped to fool a novice into believing the coin had no wear. Regardless, dipped coins can be tougher to learn with than undipped coins.