I'm partly just posting this to get some more content going here...
...but I've been using Rider for the past year or so, and I'm not sure I can say it's better than Visual Studio.
I find anytime it comes up it's all praise for Rider (including the debugger, which i find to be crap)
The Pros:
--IdeaVim is better than VsVim
--Feels a bit snappier
--The find in files pops up in a dialog box with "display as you type"
Cons:
--I really don't like the debugger layout. It's not customizable at all and I find I'm going back and forth between tabs all the time
--The debugger also doesn't have a second watch window, which blows my mind. (I often want to compare the state of 2 variables side by side, which is a huge pain in Rider)
--It has a bad bug where sometimes it won't recompile my changes, so I have adopted the workflow of always deliberately building before debugging, which is annoying.
--Doesn't work with WinForms
I just always see comments about how much better Rider is. It has some advantages, but it has some massive flaws IMO too. I'm not sure what I'm going to use going forward.
Right now I'm developing in rider and debugging in VS.
I swapped to using Rider about 4-5 years ago now, back when visual studio's refactoring tools just weren't quite as good. Since then, because I've learnt all of the keybindings, the layout and I've just generally become familiar with rider I've never swapped back. I'm actually not sure how caught-up visual studio is these days as I've not even bothered to look. Since it also has dotmemory and dotpeek support, it also just makes life easier for me.
As a side note, I'm pretty sure the watch window is a list of variables and you can just add to it? (Not got my PC / rider open right now, so can't check to be honest)
The issue I have with the watch window is that I want to have 2 watch windows side by side, so i can compare to separate variables side by side. For Rider I find i have to use the locals window as one of my watches which is often really cumbersome.
Honestly, what I really want is an IDE tool to give me some sort of "diff" of objects while debugging, but the 2 separate watch windows is the best I've found.