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.