Now that every supported Windows box ships with .NET, I would argue that C# + WinForms is the most convenient option to quickly put something together. And C# of the WinForms era was still recognizably a Delphi-like language with Java-like syntax.
Yes, and yes. I did Delphi and VB6 in late 90s before moving onto C#, and I remember being amused at how it was Delphi and not VB skills that transferred the most. A bunch of stuff in the .NET object model - notably, first-class properties and events - was clearly motivated by the desire to have native support for abstractions that were idiomatic in Delphi (but were done "by convention" in e.g. Java). And then WinForms itself is so much like VCL, you feel right at home.
And yeah, it is very specifically designed around rich designer support, which is also very similar to the Delphi designer in practice. Same drag-and-drop experience with controls, a property grid to edit properties and wire up events, anchor-based layout etc. Components can be designer-aware as well, plugging into the designer UX.