Button compass - Not needed. I have been to Portland a few times with last being in 2009. I found Portland an easy city to find my way around in. Depending on weather, Mt. Hood will give a good indication of direction. Also with the Columbia River to the north and the Willamette River separting downtown Portland to the west and with Highway 5 along with 99 running east/west, I cannot see how anyone who has lived there any length of time, could get that lost. Also in the aftermath of the 2011 Japan earthquake, I recall seeing on the news, entire blocks of houses and buildings destroyed but there were still plenty of traffic direction and road/street signs that were untouched. I would suspect the same happens in any quake anywhere.
Considering how little room a button compass takes and how little it weighs, I disagree.
(full-size) Leatherman - Already have a knife, a small set of standalone pliers or better yet, a 5" size vice grip is infinitely more versatile then the pliers on the Leatherman. Of all other tools on the Leatherman, what use in this scenario would they have.
I've fixed a lot of stuff with multitools. And opened a lot of silcocks. I'd sooner have those options than carry heavier tools with fewer uses.
Spare pair of well broken-in boots - A good pair of running shoes or lighweight hiking shoes is much better option. Heavy boots makes for a lot extra expended energy.
Boots don't have to be heavy and they do a much better job of protecting ones feet on broken ground than running shoes. Considering how serious the consequences could be of a foot or ankle injury, I would go with boots.
Rain poncho or jacket - [color:#3366FF]as in the list above, garbage bags can be a makeshift option.
A warm fleece - Depends on time of year. if the weather is cool enough for a fleece, chances are sister is wearing as weater or jacket to work already. Also the fleece adds bulk to a GHB.
Wet is cold. Cold is bad. Very easy to get wet and cold if stuck outdoors in Portland. I view these two items as essentials.
Signal mirror - Not needed in an urban environmen
Too light and easy to carry to not have on the off chance it's important. A mirror can also help you treat a wound on a part of your body that isn't as easy to see.
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