Thinking about signing up for $100 Windows 2008 Virtual Machine Hosting Account I am going to be running a Web Server (IIS) and ASP.NET site that taps into a SQL Server what license am I supposed to buy? Never had to pay for SQL before. Always been paid for by my company. How do CALs get factored into the situation when you are running a web server hosting pages to 1000s of users.
Would I just get the 1 processor license? That seems expensive.
Licencing can get complex, fast.
For definitive answers, you can call and speak to Microsoft about your specific situation.
There's also a Licencing Whitepaper from Microsoft, which explains this in more detail (yes, it says Hyper-V on the link, the paper also talks about SQL 2008 - see Page 11) - Sorry, DOCX format only)
That said, this is the summary, as I know it:
Who to obtain licences from
If you need an SQL Server licence on a shared hosting environment then you need to obtain the SQL Licence from your hosting provider. You do not buy a licence directly.
If you own, or lease the physical hardware, then you can either buy the licences outright, or obtain it through your hosting provider.
Processor vs Client Licence
If this is serving content to random folks on the internet, you need Processor licences.
If this is serving content to a single client, then you can get either CALs or Processor Licences.
All that said though, if your database isn't that big, and you don't need the replication type features - you can use SQL Server 2008 Express. It's free, even for commercial use, and has almost all the same features as the higher editions - plus, when you outgrow it, it's a seamless upgrade (just install the full version and mount the DB in the full instance)
If you're getting a hosting account, many hosters allow you to 'rent' a SQL box or space on a SQL box without you having to buy a license. Depending on your requirements, that may be far cheaper. You'd face some restrictions as to how to use that though, and usually relatively limited in space (think ~50MB for ~$25 a month).
If you're more interested in running your own server, through hosters you can get SQL Server 2008 Web Edition, which would certainly be much cheaper than buying a per proc license for Standard. I believe Web Edition is offered by hosters for a monthly fee of ~$30.
Web Edition does not have all the functionality of Standard or Enterprise, but depending on your requirements might be more than enough.
Hope that helps.