Practice makes perfect. I think people harping on him like this is his 5th year in the NBA and he hasn't figured it out is a good probably not a bad thing.
See the column "Close Shots" here, which was referenced in the original article. When it was written Damian was at 20%. It's apparently fallen now to 11.1%. He only takes .2 of these shots per game, according to that site, so maybe it's not the end of the world. I think most of the time he takes those shots he draws contact and he misses but gets to the foul line so it may not count against him. Some guys like Tony Parker and Zach Randolph have a gift for getting in crazy little angle shots under the hoop no matter how congested it seems to get. Lillard clearly does not have that gift. This isn't really a floater issue for him, since the definition on the site of a "close shot" is a shot taken within 12 feet of the basket excluding drives. They are the tricky nifty little shots and the lobs that guys make when a teammate finds them near the rim. It's not the most critical thing in the world for a point guard to master, but it speaks to his lack of touch around the rim.
Yeah, I think it's because he's got the ball at the top of the key and is dribbling into the paint. He can survey the floor and the clock and the spacing and time things perfectly. He's not worried about his "roll" man on the pick and roll--he's just got to think through exactly how to get his own shot with less than a second or two left. That clarity of focus and the heightened tension of competition seems to play to his strengths.
True hoop TV talking Lillard. Front Page on ESPN, sophomore rankings for the month: Lillard #1. Lillard gets flack for not being an MVP finisher at the rim, and not being the biggest, strongest, most athletic PG in the NBA, but Thorp had a nice take on his "mini-step-back 3." http://espn.go.com/video/clip?id=espn:10153025