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Assuming existing software on the iLiad (no significant upgrades), the iLiad is already as good as it will get and the little we have seen of the DR software appears to be a significant advance - and it will get better still over time. Unless you have a specific (existing) application in mind for the iLiad WiFi, it will probably not meet your expectations.
So, the real comparison is between the 1000S and the 1000WS. I don't think there is any doubt that WiFi and Bluetooth are a huge help to developers of software for the DR (allows remote login or an attached keyboard). If iRex (or a 3rd party) can come up with a usable web browser for the DR then it will be worth while for a wider audience. In a business context, opening up iDS delivery means again that WiFi is worthwhile. Based on the iLiad, I doubt most people will miss the WiFi if they buy the 1000S, but iRex could surprise us.
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