Modern bottom brackets use a sealed bearing type construction that keeps water and debris locked out, so they seldom go wrong. Maintenance is impossible so they need replacing when they do wear out. Older style cup bottom brackets need to be re-greased every now and again, and occasionally will need to have their bearings replaced. There are a lot more teeth on the chainring cogs than those on the rear cassette, so need changing less regularly. Cranks usually a solid one piece construction so there is not much to go wrong.
The thumb test is the fine art of pressing on the tube with your thumb to see if it’s inflated. During testing, I took a pressure reading out of curiosity, and to the touch, road tires feel fully inflated around 30 psi. How pathetically sad—30 psi!—when you’re probably trying to reach at least 60 psi on a mountain bike, 70 or more on a hybrid, and it only goes up from there.
Where to begin?! Long story made somewhat short. I bookmarked this place because I saw their dog Kaya and was sold. Lol. But they had 5 stars too so that helped. Amazing people. Very down-to-earth. Took the bikes down the path to Discovery Park. If you're in-shape and do mild cardio, then it should be an ok ride. I don't do cardio and I found myself trying to sell my soul like 15 times just to get to the top of some hills. Lol. Made it to the Ballard locks and actually got to see a boat pass through! This is the off-season so not much boat traffic. Steve, an engineer we met there, said peak time will start in May. Ate lunch at Ann's in Ballard. Delish shrimp sate! I busted my tire in a pothole and had to make a trip to REI. Which wasn't awful because we wanted to go there anyway. The city was tough to ride in at 5:00pm and we rode the sidewalk most of the way back due to the congestion. Some pedestrians are obvious to you and I almost ran over a few people.. By choice. Lol. Made it back right before they closed at 6:00pm. Easy peasy! Notes: Take some water. Take some pictures. The ride is beautiful so don't rush through. Get there before noon to give yourself some time to cruise.
Our favorite hand pump for commuters is the Lezyne Sport Drive HP, and you can read more specifics about why in our full-length guide, written by Dave Yasuda, a writer and tester with over 30 years in the saddle. To sum it up, Lezyne makes pumps with an extendable rubber tube that connects to your tire valve, and that’s the difference between awkward and demoralizing. It’s not the only company that does so, but it is one of the few, and it does it the best. The Sport Drive HP can adapt to any tire valve, has no small fussy parts to lose, and inflates more easily to higher psi levels than anything we tested without floor leverage.
Basically, you’re stuck with toggling between systems for the advantage of a few pumps, and it doesn’t seem worth it. In the original iteration of this guide, I tested 12 pumps and inflated three different tires completely full to their psi rating, and measured how many pumps it took. Yasuda did similarly for his revamped full-length exploration. That’s 36 tires, and I can guarantee there is no difference between 50 pumps and 100—it’s all terrible.
A pair of disposable latex gloves:  Not absolutely necessary, but good for keeping grease and grime off your hands during a repair.  Also, nice to have in an emergency when it starts raining and the temperature drops 20 degrees and you don’t have a pair of regular gloves.   Just keeping your hands dry and the wind from directly blowing on them makes a huge difference in comfort.
As you mentioned, it is surprising how often you can get multiple flat tires on while riding, particularly on longer sprints. The tip about bringing a patch kit in your bike repair kit can be incredibly helpful if you’ve already had one flat tire. I agree that all you listed seems like an awful lot to carry, but it’s always better to be safe than sorry, isn’t it?

Bike Radar gives the Pedro’s levers 4.55 out of five stars and claims they’re the “best out there.” (Can we pause to admire the extra five hundredths of a star the site chose to award it? Very specific.) Aaron Gulley, writing for Outside, states, “I can’t count the number of times I’ve snapped cheap plastic sticks, shredded my hand in the process, stomped around cursing in pain for 10 minutes, and then, insult to injury, been tool-less and unable to get my tire off anyway. That will never happen with Pedro’s.”

Brakes come in a variety of designs depending on the age and style of your bike. Rim brakes offer more modulation but have less stopping power, so are more suited to riding on the roads. Disc brakes can provide huge amounts of stopping power so are best suited to off road riding, although ‘V’ rim brakes are also well suited to mountain biking. All brakes use a friction system to stop the movement of the wheel, so regular checks of the contact pads should form part of your regular cycle maintenance.
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