We like, and recommend, the Crankbrothers Speedier Lever. If you have to pick only one, go with the Pedro’s, but if you want a backup or have some hard tires to unseat, Crankbrothers is a great choice. It’s only one lever (as opposed to a set of two, like the Pedro’s) and it’s longer, so we didn’t pick it over the Pedro’s for portability reasons. But it’s an excellent tool. It has a wide handle you can grip with your whole hand. Like the Pedro’s, the tip is the right size and shape to prevent slipping and stay in place, and the shape of the handle happens to protect your knuckles if you do slip. Even in situations where I didn’t need it, I liked having it because it made me feel like a pro.
Let me go ahead and get the bad stuff out of the way. First of all, this stand is NOT the same level of quality as something you would find in a bicycle shop being used for the shop's repairs. it's quite a bit more flimsy, and the grip likes to rotate if you don't get the bike's center of gravity just right. The tool tray is also made out of a rather cheap plastic that can break easily at the rim. That being said, this stand is perfect for home users and makes mundane tasks like fixing a flat or cleaning the chain much easier. It easily holds my Raleigh Merit 3, and I don't worry about the thing falling even if the grip tilts a bit. The stand significantly shortened the time I needed to change an inner tube on my bicycle, and made me less worried about damaging something on the bike by jury-rigging a stand out of whatever I had lying around.
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.
3D Printers Baby Bath Tub Baby Strollers Bar Stool Bean Bag Chair best actor Bike cover Blackhead Remover Boys' Boxer Underwear Car Chargers Ceiling Fans Chair Cushions cleaner Dining Chair Diving Masks Elbow Braces Electric Air Fryer Electric Stove Fizik Saddles Folding Ladders gas cooktop Handheld CB Radio inflatable boat Kindle Paperwhite Makeup Brush Makeup Chairs Men's Cycling Shoes Paper Towel Holder Ping Pong Paddles pool cue rack Preqnancy body pillow Projector Stands RC Helicopter robot rocking horse Seagrass Rug Small Indoor Dog House sound bars Table Round toddler travel bed vacuum Vanity Makeup Mirrors Walmart Folding Table Women's Condoms Wood Table Lamps
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! 

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.
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.
We like, and recommend, the Crankbrothers Speedier Lever. If you have to pick only one, go with the Pedro’s, but if you want a backup or have some hard tires to unseat, Crankbrothers is a great choice. It’s only one lever (as opposed to a set of two, like the Pedro’s) and it’s longer, so we didn’t pick it over the Pedro’s for portability reasons. But it’s an excellent tool. It has a wide handle you can grip with your whole hand. Like the Pedro’s, the tip is the right size and shape to prevent slipping and stay in place, and the shape of the handle happens to protect your knuckles if you do slip. Even in situations where I didn’t need it, I liked having it because it made me feel like a pro.

Patch kit:   Patch kits are easy to use, light and compact, and if you get more than one flat on a ride (it happens more than you’d expect), it can save you when you’ve already used your spare tube.   Plus, on a rear wheel, patching a tube can be faster than replacing it, as you can often do this without removing the wheel at all.  Another upcoming post is going to show you how to patch a tube.
To pick the right size bicycle, you want to measure your height, and specifically your inseam (inside leg), in proportion to the size of the bike frame. The inseam measurement determines the seat height, or the “stack.” Next, you must calculate the “reach,” which is the horizontal distance between the bottom of the frame and the head of the bike -- or, in layman’s terms, the distance between seat and handlebars.
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.
×