I have a similar problem. I am sorting and have a maximum on retunred results. Works fine on my SQL Server computer but appears to timeout on another server using MSDE.
Dim sorter As New SD.LLBLGen.Pro.ORMSupportClasses.SortExpression()
sorter.Add(New SD.LLBLGen.Pro.ORMSupportClasses.SortClause(EntityFieldFactory.Create( SBH.Logging.Dal.TblLogFieldIndex.LogId), SD.LLBLGen.Pro.ORMSupportClasses.SortOperator.Descending))
Me.TblLogCollection1.GetMulti(nothing, 100, sorter)
If i try to return TOP results then it timesout but will work fine if i set MAXIMUM rows to 0!