Holy smokes, Fred! Windows Paint got a little better over the years but it's still a piece of junk.
I do this sort of annotation almost daily in my work. But I use
Paint.NET because it's actually a real image editor and it is much,
much faster than other tools. So even though I own Photoshop and Photoshop Elements, I always use Paint.NET for handling annotation on screen captures.
I admit that I used to use Windows Paint. Once I found Paint.NET many years ago, I stopped.
Oops, did I mention that Paint.NET is free?