choose C# + Sql Server a good first step , be interested in Craig's experience in other top-level choices. If u are contracting out the job , it might depend on what the "shop " does , but a factor to consider might be , when all this is done , do u plan to have your in-house guy maintain it . If so , these might be considerations
1) WinForms versus WPF. WinForms very similar to old style VB , WPF more geared to fancy graphics, but u need to learn XAML and Blend.
2) 3rd party contrls like DevExpress. They add fancy graphics instead of battle-ship grey , but measns yr in-house guy has to learn them , + u have to buy dev license etc of u want maintain in-house.
3) 3rd party frameworks like nHibernate , again if the 'shop' uses them , that is easy for them , but very difficult for your in-house guy.
So as u can guess , my bet would be keep it sinple , WinForms , no fancy 3rd party additions