Sauron should have won!

[Mungo of Bracegirdle]

I think we all can agree to an answer to the first question posted; but, I find the second question much more interesting. Once the Ring was destroyed, so was Sauron. We can agree on this. Sauron's armies on the other hand were not. The catch here is that Sauron's will and malice was bent over them. This meant as soon as he disappeared, so did his armies driving force. This is why, once Gollum falls into the Cracks of Doom; Sauron's forces are pretty much reduced to nothing but sitting ducks. One of my favorite passages in the books is:

From all his policies and webs of fear and treachery, from all his stratagems and wars his mind shook free; and throughout his realm a tremor ran, his slaves quailed, and his armies halted, and his captains suddenly steerless, bereft of will, wavered and despaired. For they were forgotten.

This is right after Frodo puts on the Ring. If the simple fact that when Sauron turned his mind, malice, will towards capturing Frodo made the entire of his empire halt, then imagine what would happen if his will were removed completely. This is why I think JRRT is a master word smith. Look at this passage; only two sentences. One full of detail. The second only a few short words yet full of power. This is why we love his literature.

Cheers,
Mungo