I had problems with configuring wine prefix manually. Some frameworks could be downloaded / installed. With some were problems. 32 bit wine worked, but 64 bit prefix did not most of the times.

There were attempts to auto configure apps, like bottles program. This did work quite well when I used it for simple programs.

As with Linux. It takes some time to get familiar. Once you set up everything correctly, it will just work.

I've never tried it, but my impression from other people is that it's unreliable and maybe doesn't even work at all for the newest versions of Microsoft Office.