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I don't see planting a fake plane crash as being Ben's style. He works in the arena of mind games and character manipulation. And while we have a hint that he's got a lot of financial resources and a people network in the real world it doesn't strike me as being anything like the resources Widmore might have access to. Ben might have also thought he had the island locked down tight by disrupting communications to keep it hidden and by the time he realized the island was compromised by folks like Naomi from the freighter that would have happened after the plane wreckage was found. Besides, the freighter was already near the island and had apparently been there for some time despite the fact they already seem to have the fake flight recorder from the staged crash. (Or is it the flight recorder from the actual crash on the island?????) If Ben wanted Michael to be on the freighter that would have already been part of his plan way back when he let Michael and Walt leave the island on the heading of 325 before the flash. If Ben planted the crash wouldn't it be more likely that Widmore realized it was fake and it helped him to actually find the island? So much for a good staged crash if you're Ben and you forget to put data on the recorder that would keep people away from the island or to fool them. How omniscient is Ben though? If he can see into the future and the past he might be able to set up critical situations like the staged plane but I'm not convinced he is that much of a visionary, or that he communes well enough with Jacob to get such information, or that he would have screwed up by putting incorrect data on the flight recorder. It is possible the data recorder the freighter captain had was fake fake, not being from the staged or actual crash, but to what end? Some part of an elaborate cover story? Regardless, the freighter seems to be at the island after having possession of a flight recorder with knowledge of the faked crash. The bottom line is that staged crash did not keep the freighter away from the island. But do the frieghter people work for Widmore? Maybe maybe not.

Widmore is a highly driven type AAA personality and would probably go to great extremes to achieve his goals. But as with Ben we don't really know what Widmore wants with the island. Assuming that Widmore wants access to the island why would he have a need to plant a crash? My guess is that the primary reason was to terminate all searches for the crashed plane. With enough planes and boats looking for the crash, combined with modern technology, it is possible that the likelihood of someone stumbling upon the island would be greater than in the past? We had a hint of Amelia Earhart being somehow linked to the island through the use of Herarat Aviation. Is it possible that during that search someone accidentally found the island and revealed some of it's mysterys to secret powerful organizations or high powered secretive corporations? (Yeah, I wouldn't be surprised if someone who appeared to be young and unaging ended up being Amelia Earhart's co-pilot...) The issue of the Black Rock log is probably very critical to this entire issue, seeing as Widmore bought it at auction. It may have left the island with a few survivors from the Black Rock in a lifeboat. Any secrets in the log could be related to strange happenings on the island or how to get to it or leave it. Sure, the log entries might have seemed crazy and chalked up to sailors that had gone nutty while being stranded on the island when in fact they went nutty because they didn't know how to leave the island properly at the time. So anyone reading the journal might have thought log entries in there were just the ravings of a lunatic(s). Alternately the journal might have been brought back to the real world by someone who later got stranded on the island because of the Amelia Earhart search.

Regardless the giant question is what's so important about the island and what might be the big draw for someone like Widmore? My guess is something like the age old stories of a fountain of youth. True or not, Widmore might think that getting to the island or learning its secrets could give him eternal life. Someone with that much power and wealth might feel entitled to it and spend anything to find it. The search for a fountain of youth is an age old story among explorers throughout history so I wouldn't put it past the writers to use such a story element. Is there a geographic relationship between the island and the healing places in the real world? Maybe!