For the budding mechanic:  A good pocket sized repair guide.   One good option is the “Pocket Guide to Emergency Bicycle Repair”  by Ron Cordes and Eric Grove.   It’s only 3.5×4.5 inches and a half inch thick.   I don’t carry this myself, but for someone who’s new to this whole bike repair business, it’s really helpful to have. A future blog post will cover this book in detail.

The Pedro’s lever slipped only once throughout testing, though that may have been my fault because I was spaced out after changing 16 different tires. So they’re not foolproof, but they are far and away more reliable than the next closest competitor, from Park Tool, because the small, rounded tip on that one is hard to keep seated under the tire. Not impossible, but I wouldn’t choose it over Pedro’s.

I just got a tune up on my bike and it rides so much better now! It takes half as much effort to petal, it is like a new bike. The guys who work there are so nice and always make you feel like your time is important. They don't overcharge or sell you things you don't need. I thought for sure I needed a new chain, but as it turns out, it's fine! He gave me some extra foam for my bike helmet, free of charge! I'll definitely come back here for all my bike needs!

Don’t rely on others. “People need to recognize that now there are different cassette sizes, so there are different chains depending on what gear you have. A lot of people are like, ‘Oh my friend is always prepared they always have the stuff, I’m not going to bring anything.’ All of the stuff now is very bike-specific, and you have to have your own package of stuff.”
Road riders need lightweight, tiny tools that can fit into jersey pockets. A lot of those items are made of carbon fiber, which is lighter than aluminum. Other iconic trappings of road riding, like CO2 cartridges and spandex outfits, are also geared toward minimalism, but all of that downsizing comes at a cost. Commuters don’t have to be as concerned with weight, so unless you covet something specific, don’t spend the extra money.
Over the years, I’ve come across plenty of articles that claim to tell you how to build up your cycling toolkit for cheap. Somehow the word “cheap” stops recurring in the long list of “essential” bike repair bits and pieces. The truth is, there is no real way to build a whole shop of tools all at once without plopping down a few hundred bucks. But in an attempt to show everyone that not all of us truly need a full complement of bike tools, I present the truest, most budget-conscious, and barest of bones options to you.
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.
These are some great ideas, especially the simple ones like bringing a garbage bag. That’s something so easy and cheap that it’s easy to forget entirely, but as you say, it can make a huge difference in the right circumstances. It’s also good that you discuss some minor bike repairs. That’s another thing that can salvage or destroy your ride. You want to be as prepared as possible for the best possible experience.

I bought this book to supplement "Anybody's Bike Book" because I always like to get a second opinion. This book uses photos extensively rather than drawings as in the other book. They are well composed and quite helpful providing additional detailed information in a clear, conciseful manner. Information is provided in heirarchy format and geared from initial purchase to daily maintenance of my two wheeled friend. Good book!
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.