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Differences in SQL 2008 Versions?

I am getting two dedicated servers setup for web hosting.  One for the web server and one for the SQL server.  I am trying to figure out the cost difference between leasing a license from the provider and buying my own license.  Obviously everyone would like to get the Enterprise version, but will the workgroup or other version have most of the needed features?  Will I be regretting not have features of standard or enterprise as the databases grow?  I am not creating a site like eBay where i will be storing billions of records.  I just want to see if I can control costs at the beginning of the life cycle.

Any input would be appreciated if the base versions will do the job and not lack in major needed features.

Thanks
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What about the Web edition? It seems like it has alot of the features needed, is there anything there that would be bad for me to use that.  Also, I see a big price difference between 2008 server and the R2 version?  Is there a major difference there?
I have not used the Web Edition to verify pricing differences between it and Standard, but if provided by your hosting provider and meets your needs it should be a good alternative to SQL Express as it appears to be tailored to high availability in web environments.  Having this optimized to your exact needs is never a bad thing.