If you're not part of the solution, you're part of the precipitate.
Art, did you carry pepper spray for the sharks or just clobber them with your U-lock? Also I bet it was pretty easy to stop for those water breaks you like.
"Think Outside the Cage"
On top of a good range of gears, tire selection is a big factor. I was riding an MTB with 1.95 inch knobbies. I would have preferred something like a 32mm slick for city riding.
For the one really steep, really LONG hill I have to get over to get to the college where I take my classes, I leave my bicycle at the bus station at the base and take the bus over. For my have-fun go-fast stuff, I've noticed a marked improvement in my hill-climbing ability since I've started lifting weights, specifically squats, deadlifts, step ups, lunges, and Bulgarian split-squats.
Oh, and my rule is that as soon as I drop below 4 mph, I get off and walk because I can walk 4.5 mph up a hill.
2014 Specialized Dolce, 1987 Schwinn Tempo, 2012 Windsor Kensington 8
Another Seattleite here. Hills are mostly mental, the trick is to shift down early, keep your cadence up and set back a little and don't go forward with full effort.
My house is 42' above sea level and every place I need to go is up hill and most of those hills are 300-450 feet high. I do use a normal rear cassette on my main bike with a compact front (50/34 and 13/26) but I will be putting on a larger cassette the next time I need to replace the chain. But I pull cargo with my Bob trailer with that gearing.
With no trailer I tend to maintain 20mph without traffic and to do this I need about 202 Watts, at a 3% grade that same number of watts will only let me go about 11mph. The 4.5% grade I am going to climb right after I post this message will slow me down to about 7 mph at the same output. This output is about 2.5 Watts/Kg and I can at my current state of fitness maintain that output for an extended period of time If I try to kick it up to about 3Watts/Kg I burn out within an hour.
So ignoring all that fancy math the answer is to keep your effort within your sustainable power output range or remember to go slow and don't burn yourself out and remember when you go up hill you also get to go down hill at some point in the future..
I took a big old swig of the gatorskin koolaid a few years back. So I run hardshells on my one bike that only takes 700x23c tires to help reduce pinch flats and the normal 700x28c gatorskin (ultras) on my other bikes.
But any of the modern tires with breakers in them are probably fine. To be honest I size them for the potholes and not the hills
I let my breathing control my power. I breathe deeply and freely. I find a gear where my legs can convert that into a comfortably fast cadence, if I can't maintain a pace, I take a break, catch my breath and then go work on another section of hill. One important thing that I don't hear mentioned is that as you ride hills again and again, you will learn them and you body will know how to climb them. You will learn exactly where the inflection points where a street gets steeper or flatter are. You'll learn the necessary pacing.
One thing I have noticed is that if there is little or no traffic on the hill, I can usually manage it not too badly. I'm as slow as molasses on a cold winter day, but I can cycle to the top. But if there is lots of traffic, my heart rate soars and I can't do it.