Actually there are at least two questions there but I will answer them one by one:
1. Yes you can change from B2 to H1B however, there are few problems with this. One is that H1B is not available right now, you can only apply on April 1, 2010. If you make it through the possible lottery, you will need an approval. Once approved it will kick in only on Oct 1. During this entire time you have to maintain status to reach October 1. If you don't only consular processing is possible. Therefore it is logical to do a consular processing.
2. The B2 will give you more assurance of entry and you can always file for a possible change of status while the VWP is often easier, it does not allow change of status except adjustment under marriage.
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I agree with my colleague's reply. I would only clarify a couple of issues with regard to the H-1B.
You don't mention your field, nationality, or whether you have recently had an H-1B before. Some employers - universities and certain affiliates of universities - are exempt from the numerical limitation (even if you don't work in an educational role), and so you can still get an H-1B working for such an employer in the near term even though the cap has been reached (otherwise delaying the earliest H-1B start date to October 1 as stated).
Individuals from Singapore or Chile have H-1Bs reserved for them outside of the cap by treaty, while individuals from Australia have an almost identical visa - the E-3 - reserved by treaty and statute. Individuals from Mexico and Canada may have access to TNs for certain professions.
If you have had an H-1B recently and have not spent a full year abroad yet, you can still get the remainder of that H-1B without again being subject to the cap.