I use this screenshot tool (decided to give in and start using a good real screenshot program after the forum update): https://getsharex.com
Tons of options and takes a little getting used to but, man, this thing has saved me so much time since I got it it’s unreal.
Now I just hit printscreen, use the keyboard shortcuts for the tool that has various tools to crop, draw arrows, colored rectangles, whatever and then i just click copy and paste it right into the editor here. Love it.
I mean, I could just use the rectangles/circles from paint, but too lazy to do that 
Exactly why that tool is right up your alley. Install it then hit printscreen and it instantly gives you a screen to edit. Instantly. Then you click copy and then paste it in. Takes me seconds now to take screens and quickly edit it up.
Don’t underestimate my MS Paint skills
You still have to draw boxes…
What I need is an AI like Jarvis 
Lol you poor thing you.
Doesn’t look like that allows you to save a image to your PC. And since most of my shots are ingame probably not better than good old Paint for me.
But this is off topic.
It absolutely does allow you to do so.
I use Snipping Tool (installed by default with Win 7 at least. Don’t know about Win 10). It got everything I need. Very convenient. Got pensils/ Highlighting tools as well. Try to find it in the start Menu 