I have noticed that in this woot-off they have repeated the same items a couple of times. Is this a new thing or do are they really making it obvious that they just want to get rid of a certain item?

This is a long-standing woot tradition. I don't know exactly how many years it goes back, but the most obvious times are in the comment threads. "YOU JUST HAD THIS FOR $5 BUCKS MORE, WHY DID I BUY IT AT THAT PRICE WHEN I COULD'VE GOTTEN IT CHEAPER IF I'D WAITED?!"

I can't say for sure there aren't some items repeated, but usually it's not actually the same item being repeated.

For example:
http://www.woot.com/offers/gunnar-stylus-computer-gaming-eyewear

http://www.woot.com/offers/gunnar-rayne-adv-computer-gaming-eyewear

http://www.woot.com/offers/gunnar-bitsurfer-computer-gaming-eyewear

At a glance you might think it was the same item 3 times over the Woot-Off, but it's actually 3 different models.

What TT said. Plus it also helps cut back on the people complaining because an item is up for too long.