This can definitely depend on the technology and the use case. For instance, I'm building a .NET desktop application and started using WinForms since I have several years experience with it. I scrapped that and started using XAML for the first time and I am already more productive in XAML than I am with Winforms. I have a cleaner UI and an easier time with the architecture due to the data binding.
My point is that there are technologies that if you are using a technology that is a pain in the ass (Winforms) but that is all you know moving to a newer technology that has been designed to be easier to use can not only benefit what you are building but even save you time in the long run.
My point is that there are technologies that if you are using a technology that is a pain in the ass (Winforms) but that is all you know moving to a newer technology that has been designed to be easier to use can not only benefit what you are building but even save you time in the long run.