We focused on tools that would be useful to a commuter—someone trying to use a bike as a functional way to get around town, as opposed to riding recreationally (road biking and mountain biking). That said, it’s a wild and wooly bicycling world out there, and the streets are packed with so many different bikes, all shapes and sizes, new and old. Customizing your flat-fixing kit has advantages over buying a preassembled kit that always contains a tool (or two or three) that’s a piece of junk, or you don’t need. Or it’s missing something you do need. If you build your own kit, at least you know everything works. And you can add only what’s necessary for your specific bike without ending up with stuff you don’t need.
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?
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.
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.
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.