If you are planning on going on a multi-day ride or just riding a long distance in a day, you should have something for first aid, just in case. Unfortunately, almost everyone who cycles frequently will go down at least once in their life. This kit can be really small and compact and can include bandages, some gauze, and a small bottle of a disinfectant.
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!
Yes, bicycle shops generally provide repair services. A typical list of offered services includes regular service/adjustment (including safety check; and brake, drivetrain, and tire inspection); premium, and annual service, which is a more extensive tune-up. More specific repairs include drivetrain tune-up, brake system tune-up, flat tire fixes, brake repairs, cleaning and touching up the bike frame.
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?
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.
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.”
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.
In addition to the Rema patches, put a new tire tube in your kit. The best method for dealing with a flat roadside is to swap out the tube and save the task of patching for later. If you’re not sure what size your tires are, it’s printed on the sidewall of the tire. This inner-tube buying guide has some photos of where to look. What brand is almost irrelevant as many tubes get manufactured in the same place, so whatever your local shop has behind the counter for under $10 will work fine. The only reason to spend more would be to save weight.
Man, if you're starting out and you know you'll need several components for a bag... just get this. It will save you so much time picking everything out that even if you balk at the price (amazing value, by the way) I bet that if you did the math using your hourly wage and the time spent picking everything out and making sure it fits... you'd save a lot of money and a lot of irritation if you just got this. Just get this.
Whether you ride a single, 7, or 10 speed bike or anything in between, you will need a slightly different chain. The major difference is that they come in varying widths to accomodate the different spaces between the gears, but quality of construction is also a factor in choosing a chain. Inspecing the chain should be a part of your regular cycle maintenance procedure- It’s important to keep a chain well lubricated, but oil will also attract dirt and so different oils for specific riding conditions are available. Remember to clean your chain regularly to get the longest life out of it and the gears.