In my experience, a Chicago shine is really something to talk about. They seem to be the most conscientious shoe shiners of any city. So, I'm not surprised we've actually now devoted a thread to the Chicago shine.
Go for it.
Brown is an outstanding suit color, and you'll be surprised by how versatile it is. If you want it to be timeless, I'd stay away from fashion forward or trendy features, like the narrow lapels. But, to each his own.
The G&G bespokes are such a cut above everything else I own that, considering how many pairs of shoes I already own, I think I'm spoiled for bespoke and will try to stick to that going forward.
It will mean fewer shoes, but a pair a year is about all I'd need.
(Funny, but I think your avator might enjoy my monks.)