Mini Pump:   This actually goes on the frame of your bike, as it’s a bit too big for most under-seat bags.   Coming soon, we’ll have a review from Bill of his very favorite one, but a good pump is a lifesaver.    Some people instead carry a CO2 inflator, which is faster and easier to use but does require disposable cartridges, and each time you have a flat, you’ll need at least 2 of those cartridges.  There are combined pump/inflator tools that we’ll also talk about soon.
Keychain style flashlight or headlamp, LED type, not incandescent:   The keychain style is tiny and lightweight, the headlamp style is a bit bulkier but easier to use.    You can get these for a couple of bucks or less at the local big box hardware store.  The LED ones are lighter, more durable and last considerably longer.   Very useful if you need to make a repair after dark!  I keep a keychain style one as a backup as I normally have a headlamp in my backpack.
Do not take your Bike to Kyle's Bike Shop they handled my bike so poorly they can not work on Vintage Schwinn' and the attitude they had if it wasn't a high dollar bike don't expect good service. I had to find my own parts, had to take the bike back twice to get the wheel trued and they ruined my bike it is so scrapped up the Schwinn is gone on the side of the bike. If you care about your bike do not take it here.
Many bikes, including older models and track bikes, have bolts attaching the wheels to the frame instead of quick-release levers. If your wheels are bolted on, in most cases you’ll need a 15 mm wrench to remove it. We didn’t test wrenches, because there aren’t that many tiny 15 mm wrenches, but the GearWrench 15mm 12-Point Stubby Combination Wrench is perfect for stuffing into a flat kit and Amazon reviewers seem to think the same. Our experts also recommended the Surly Jethro Tule, but it’s expensive and harder to find.

These folks took me in right away, diagnosed and fixed my stripped handle bar clamps and had me on my way to work in about 15 minutes. Friendly, straightforward, understands the rider's objectives (in my case, how do I get home from work). Not to mention, the fee was reasonable. I have been in many bike repair places in my 6 decades. This is the best.
Main types of bicycles are road, mountain, commuter/comfort and fitness bikes. There are more specific types and other names for bike types within that, such as urban bikes (same as commuter bikes), cruiser bikes, dual-sport bikes, hybrid bikes, fixed-gear bikes, cyclo-cross bikes, adventure road bikes (aka  all-road bikes, gravel bikes), road bikes, touring bikes and specialty bikes, like BMX.
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!

It has some useful information for basic repairs... not so heavy on the maintenance side but there is some in there. The pictures and drawings are in black and white, but mostly visible. Only a few are difficult to see. However, they are in 2-dimensions and they don't show you HOW to do the thing, they only show you the general area and the part you want to manipulate. The phrasing in the instructions can be hard to follow without a good visual reference unless you're already a master bike mechanic (which you aren't if you're thinking about buying this). So, buy this for general reference and rely on Youtube for video. The two together are better than either one alone.

These guys are awesome. After work, I got to my bike to discover my back tire was completely flat. It had a slow leak, so I was able to pump it up enough to make it to their shop. I got there 10 minutes before closing and they were able to fit me in. They replaced my tube and picked all of the glass shards out of my tire. Awesome customer service and they saved me from having to do this myself in the dark and the cold.
Next to everything else that might go wrong with a bicycle on an extended ride, a flat is a relatively minor issue that can be easily repaired trailside, if the right tools are at hand. If they aren’t, a quick fix can turn into a long walk. Well-prepared riders will perform a tune-up regularly and clean their bikes after every ride. For the less-diligent, a well-stocked repair kit will suffice.
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?
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