This isn't gonna affect the rich at all, lol. You don't know where the rich live. The nice house up the street you're talking about robbing, that's not a plutocrat. That's just the local doctor. Still working class, just a bit better off.

Rainy/snowy nights are excellent opportunities.

Can confirm. Used to be a security guard. On rainy/foggy nights, exterior camera lenses tend to get wet and blurry and the cameras can't see shit. They'll be able to maybe tell that someone was there, but they won't be able to make out any significant details. (Interior cameras will be unaffected, of course, so be careful of those.)

Extra bonus tip: wear a disguise! Just a wig and glasses or something can make you look like a totally different person. It may not fool people face-to-face, but it's much easier to fool a grainy security camera picture. And if you have short, dark hair while the police are looking for someone with long, blonde hair, they're very unlikely to ever figure out it was you.

Read about Italian illegalists for inspiration

Renzo Novatore's wiki page is a great start