> I was also pretty pleased with my move to MacOS but one thing I really miss is the file navigation from Windows. Like when I want to drag a file somewhere a few difectories deep. I wish I could hold it over a folder and then have it open that next folder and so on. Is there a way to enable this?

Macs have had a feature like that since the 90s called spring loaded folders. Pick up the file you want to move, then hold it over the base level destination folder for a moment until it “blinks” and it’ll open the folder in a new window. Rinse and repeat as you’re drilling down to the folder you want, then drop.

Back/forward buttons in Finder windows can also be hovered over with a dragged file to trigger those.

> Also the in application file picker makes it difficult to go up and down directories.

You can use Command up or down keys.