One is better than none, and NO ONE can foresee the future.
I don't think I'll even need one, let alone two, but it's better to be safe than sorry.
I do as close as I can to carrying here, I keep a handgun in it's box in my truck with 3 full mags and when I go into work I bring the whole thing.
Technically I can fanny-pack carry due to the relatively simple transportation laws here, but it isn't the wisest thing to do and from what I hear most cops will arrest first, settle later, and most likely confiscate the weapon indefinitely and I can't afford that.
Yeah, I wouldn't do anything risky, gun-wise in Illinois. They're way too anti-gun to even think about doing something at the edges of the law. I highly doubt they'd care if you found a loophole and used it, they'd still do their best to make your life a living hell and to try and use you as an example as to why guns are such horrible evil things that need to be destroyed.