All multi-tools are not created equal, but most with a plethora of features will get plenty of the jobs done. I personally like, and use often, the Lezyne RAP-21 LED tool, which will run you around $30. I like it because not only is it a high quality construction, but it has just about everything you’ll need, plus a sweet mini light. This will give you a chain breaker, spoke wrench, disc brake wedge, and all the most often used Allen keys and drivers. We’re talking a decent number of tools for 1/4 of what they would cost buying them separately.
Maintenance is the best prevention. “Prevention is the best medicine, and if you’re taking care of your equipment it’s super key. Bikes don’t just fail. If they’re in really good working condition and you clean them at night, and you’re religious about it, bikes are kind of like cars — they’ll start talking to you if something is getting worn or getting creaky or needs to be replaced.”
The Bicycle Repair Shop does rentals by the hour or by the day. They have reasonable rates. They have solid, lightweight hybrid bikes so you can tackle train tracks and brick streets and hills. They also have road bikes for the more experienced. You can reserve online in advance. You get a helmet and a lock with your rental. The staff in the shop are friendly and will suggest routes and point out hills if you're new to the area. And believe me these hills are no joke!
Be organized. “I like having everything be really small and super organized. I put all of my tools in CamelBak’s Tool Roll. It’s got little compartments, and I can separate tire changing stuff in one place, stuff like extra pedal cleats or an extra derailleur hanger in another, and it all rolls up into this tidy pouch. If I do have a repair, I can pull that one thing out and lay it out on the ground and it’s easy to work.”
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.
A two-stage hand pump tries to marry the best features of both types of pumps: the quick inflation of high volume that can achieve the higher psi ranges of high pressure. But to steal a quote from our floor pump guide, “You pump eight times or you pump 10 times—what does it matter?” That’s a quote from Daimeon Shanks, who at the time was a mechanic for the Garmin-Sharp pro tour team—that’s right, Tour de France, baby.
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.
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