Quick reply to just one of your many questions:
Your greasy wheel is because the dust cap flew off. There are 2 styles, one has a rubber cap in the middle that you can remove to get to the zerk fitting and add grease. The other is just a smooth dome. You probably want to get the first kind. Search for "Dexter dust cap" on amazon to see what they look like.
Oddly, every time I have my trailer serviced by pros, the dust caps are likely fly off on the next trip. I carry spares, and need to remember to hammer them in better when I get it back from service.
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