I like some of these bags and seem to have the same issue with pockets. They are either too big or two small. Too big is preferable, all you need is smaller bags to separate items. Too small is a non-starter.
Regarding umbrellas, think instant shelter. I don't carry one either here in SOCAL, but the one I currently own was purchased during a major thunderstorm when I lived in VA a long time back. It wasn't cheap, but is really well made. A small well made collapsible umbrella should be a consideration for areas where rain is often in the forecast.
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Better is the Enemy of Good Enough.
Okay, what’s your point??