As far as the encryption is concerned, why try to reinvent the wheel? Just connect to the webservice over SSL - it'll most likely be much safer than a homegrown alternative.
I would probably create a custom struct/object and send an array of those to the webservice rather than a DataSet. It will mean (slightly) less network traffic; it will make the webservice's WSDL more descriptive; and it will make it easier for any non-Microsoft apps to talk to the webservice, if that becomes necessary in the future.
EDIT: An example...
At the server-side you can declare a custom type (eg, ExampleUser), and then setup your method to accept an array of that type instead of a DataSet:
[WebService(Namespace="http://example.yourdomain.com/ExampleWebService/")]
public class ExampleWebService : System.Web.Services.WebService
{
// this is your custom type
public class ExampleUser
{
public int UserID { get; set; }
public string Name { get; set; }
public DateTime DateOfBirth { get; set; }
}
// this is your method
// accepts an array of ExampleUser rather than a DataSet
[WebMethod]
public void UploadUsers(ExampleUser[] usersArray)
{
// do something...
}
}
In the client application you would add a reference to the webservice. This will enable you to use the ExampleUser type declared in the server-side code above.
You could then just convert your DataSet to an array of ExampleUser objects before sending it to the webservice:
// get the number of rows in the DataTable
int rowCount = yourDataSet.Tables[0].Rows.Count;
// create an array of ExampleUser with the correct capacity
ExampleWebService.ExampleUser[] usersArray =
new ExampleWebService.ExampleUser[rowCount];
// iterate through each row in the table
for (int i = 0; i < rowCount; i++)
{
DataRow dr = yourDataSet.Tables[0].Rows[i];
// create an ExampleUser object and populate it from the DataRow columns
ExampleWebService.ExampleUser eu = new ExampleWebService.ExampleUser();
eu.UserID = (int)dr["User_ID"];
eu.Name = (string)dr["Name"];
eu.DateOfBirth = (DateTime)dr["Date_Of_Birth"];
// add the ExampleUser object to the array
usersArray[i] = eu;
}
// the array is populated so let's call the webservice
ExampleWebService.UploadUsers(usersArray);
EDIT: Another example...
If you're using .NET 3.5 then you can get the client-side down to just a few lines of code by using LINQ and object initialisers to create your array:
// create and populate the array
ExampleWebService.ExampleUser[] usersArray =
yourDataSet.Tables[0].AsEnumerable().Select
(
s => new ExampleWebService.ExampleUser()
{
UserID = (int)s["User_ID"],
Name = (string)s["Name"],
DateOfBirth = (DateTime)s["Date_Of_Birth"]
}
).ToArray();
// the array is populated so let's call the webservice
ExampleWebService.UploadUsers(usersArray);