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if you are going full rain-gear, it would include either making your only bike all-weather compatible (full fenders, etc) with the understanding that it will be clunkier to ride and will deteriorate more quickly (rust, sand, drive train, brakes). if you can swing it, get a beater bike that is specifically set up for rain and keep your nice bike (if your bike is nice) in fair weather condition.

 

carry a basic toolkit (spanner, hex wrench multi tool, spoke wrench, tire levers) and a spare tube or two. unless you want to carry a small handpump, you could invest in some CO2 cartridges and a small inflator. include some elastics, bungees, and a small roll of rubberized gaffer tape (just tear a strip of a few feet and roll it on itself so you have a little finger of black magic) -- the tape can be used for many things, from lashing something to your frame to layering up and booting a tire puncture. last but not least, buy a box of rubber gloves, and keep a few pairs rolled up in your kit. all of this can fit in a small saddlebag, handlebar bag, or hip pouch.

 

along with your standard toolkit and flat repair/replacement kit, carry an emergency rain poncho and a pair of rubber boot covers. boot covers are especially nice if you end up getting a pair of shoes that you don't want sprayed with water and sand should you get caught in a downpour or have to ride on sticky/tacky surfaces after a rain.

 

if there is a chance you are going to be riding at night, get a rear flasher and a good headlight (a powerful LED array with multiple modes & brightnesses). good lights usually have a rechargeable external battery pack -- carry a spare battery pack or at least get a few cheap LED flashers (frog knog or similar) to keep in your toolkit as a backup.

 

one last thing that i find helpful is keeping a few drawstring backpacks rolled up in my kits, as they can really come in handy if you need to pick up or carry something (or remove some clothing) unexpectedly. when not in use they fold up smaller than a deck of cards. if you have to lock your bike up outside and have a nice saddle, you can tie one of these over it so it's not so obviously nice.

 

i didn't really answer any if your big questions with specific recommendations, or cover any basic cycling equipment (like riding gloves or bike locks), but these are little tricks or lightbulb discoveries that i've picked up over biking in the city for the past 12 or 13 years. most of the small things are non-essential, but come in very handy and can save a lot of unneeded cleanup and frustration. now i never ride without them.

http://www.amazon.com/gp/product/B009QX8B2Q/ref=oh_aui_detailpage_o08_s00?ie=UTF8&psc=1

Just ordered my second one of these. Excellent light, and the brightest I currently own. Much brighter than even my Cygolite Metro. AND it's cheap.

This is decent https://www.amazon.com/Spy-Tec-Mobius-Action-Camera/dp/B00GT2B4R6/ but a second hand GoPro is going have better image, sound and will be more waterproof.

Don't forget folks, it's now legal to purchase pepper spray in Massachusetts without a license. I think a riot control sized can such as this: https://www.amazon.com/Brand-Defense-Pepper-Spray-Magnum/dp/B06XYWPWTD would fit in a water bottle holder just perfect!

I've been very very happy with this cheap ($35) rain suit from RockBros: Rockbros High Visibility Cycling Rain Jacket Men's Windproof Rain Coat Motocycle Rain Suit Green https://www.amazon.com/dp/B073WQ68BW/ref=cm_sw_r_cp_apa_i_41naCb1P6QH74

My commute is 11 miles each way. Don't know that I'd want to go further than that in them... I'm pretty damp on the inside by the time I get home. But that's true for me for anything. They're light weight but durable. Highly highly visible. If my current set gets ripped it something, I'll buy this suite again, easily.

This guy is super cheap, lasts about 2 hours on battery, and with a good memory card, holds days worth of rides. The resolution at night is really poor, but I don't ride at night so it's never been a problem. I can read license plates going full speed and faces are really clear when I look through windows. If you're looking for a starter to see if you want a camera, I'd say this is a good one to go with.

Honestly the Fall and Spring can get pretty cold. I swear by the Pearl Izumi Lobster Gloves:

https://www.amazon.com/gp/product/B00SOMS82S/ref=oh_aui_search_detailpage?ie=UTF8&psc=1

Not cheap but very much worth it.

The airzound will save your life

10 and 14mm? I've NEVER seen hex bolts that big on a bike - they would correspond to M12 and M16 SHCS - so, half an inch diameter screws. you may be thinking of cone wrenches, which would vary based on hub manufacturer (and on older bikes, headsets).

For hex wrenches/allen keys, you don't need the fancy T handled wrenches. They're nice, but they're a luxury. If you're going cheap, just get a normal set of metric hex wrenches (like this - bonus SAE wrenches to boot http://www.amazon.com/Stanley-85-753-Piece-Long-Metric/dp/B000NIFJQE/ref=sr_1_1?ie=UTF8&qid=1405808907&sr=8-1&keywords=metric+hex+key+set ) or a folding set if you want something to take with you (but don't expect to be able to get crankarms off with it!) http://www.amazon.com/Bike-Tool-AWS-11-Metric-Folding/dp/B000OZFI76/ref=sr_1_5?ie=UTF8&qid=1405808982&sr=8-5&keywords=park+tool+folding

If you have a fancier bike with carbon components, or want to get serious about bike maintenance, do yourself and your bike a favor and buy a torque wrench and a set of hex bits. The smaller bolts with lower torques (2-5 Nm range) tend to be the ones you'll overtorque and damage parts, so start with a torque wrench with a low range first. You can add the larger torque wrench (~10-75 Nm range) later.

Other than that, just get the tools for the jobs you end up doing on your bike. A chain breaker is a must, and cone wrenches for your hub (if it uses them) are great to have.

Thanks for the reminder. It was such a whirlwind trying to get everything in BikeIndex and Garage529 and talking to the police that I forgot to put the details here.

For the Cannondale Synapse SE 105 Disc 2019 it is unfortunately a 2 month old bike so it doesn't have too much to distinguish it from a stock new bike. The only modifications that I did were reversible accessory additions like

• Shimano SPD PD-ED500 pedals
  
• gopro handlebar mount with the Cycliq Fly12 CE twist mount
  
• 2x black bottle holders
  
• Topeak Explorer Rack Without Spring with a Cycliq Fly6 camera mount attached
  
• cell phone holder on the stem
  
• Upstand bike stand
  
  The bike rack looks a little out of place compared to the rest of it as it is actually a little beat up from wear on a previous bike. It also sports a Cambridge Bicycle store sticker. Serial number MD21685
  
  For the Marin Fairfax SC4 Belt 2018 it is a little easier. It has a bike room sticker for EF Education first. It also has the same Topeak bike rack which is beat up from a car accident. The left rear side of the rack is bent in slightly. It also has one of the water bottle holders and has the normal Cycliq Fly12CE camera mount directly attached. The belt drive is also fairly unusual so I am hoping it stands out more. It also has a sticker for Farina's in Watertown and the serial number appears to be 041716870 MRN-111-01-190.

I'm on my second pair of these: https://www.amazon.com/gp/product/B004ZPRZ8Q/ref=oh_aui_search_detailpage?ie=UTF8&psc=1
(they make a regular men's version thats ~$25)

I'm on my second pair. The first pair lasted about 5 years. They roll up small and I bring them everywhere and walk around like a dork with rainpants whenever its raining, even if I'm not biking.

It depends on the u-lock. This one would be trouble for bolt cutters:

https://www.amazon.com/Kryptonite-997986-Fahgettaboudit-U-Lock-Black/dp/B000OZ9VLU

That said, no lock will stop an angle grinder ☹

Here's a great article:

http://thesweethome.com/reviews/best-bike-lock/