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The skill I find most useful but non-intuitive is to be able to turn your head over your left shoulder and assess whether it is safe to merge left, for example to get around an obstacle or to prepare for a left turn. I would practice this a lot.

Many posters here mention taking the lane, and other maneuvers. This is part of a school of thought that is both discredited and very useful known as Vehicular Cycling. The bible of Vehicular Cycling is a book called Effective Cycling by John Forester.

Vehicular cycling more or less holds that since most bicycle crashes happen as a part of crossing or turning at intersections, bike lanes make cycling less safe because they introduce more places of potential conflict between bikes and other vehicles. Thus cycling is safest when bicycles act as any other vehicle, for example taking the lane and riding with other traffic.

It is discredited because we now know that cycling becomes safer the more cyclists there are, so that motorists become used to encountering cyclists. The best way to get more cyclists is to have cycling infrastructure like bike lanes. This outweighs the benefit of reducing the points of conflict. (It's also discredited because vehicular cycling presumes that the principles of traffic engineering are good to begin with, but they're profoundly not.)

But if you talk to most experienced urban cyclists, including those who strongly advocate for bike lanes, you'll find that on a personal level most follow the vehicular cycling model. So it's good to familiarize one's self with it.

Depends what you're used to riding and where you can store it.

If you can't store it inside, you'll need a 'beater,' meaning a bike that doesn't look appealing to thieves. For most people, the best deal is going to be a 90s "mountain" bike (something like this), which is essentially comparable to a hybrid, but with 26" wheels. It's a slower-riding bike, but with the advantage of better brakes, a more upright riding position, and thicker tires for fewer flats.

If you're used to riding faster road bikes, I'd get an 80s/90s road bike (something like this), and add cross-style brakes to it (i.e., a 2nd set of brake levers on the tops of the handlebars that let you brake while riding upright in traffic).

If you can lock your bike up indoors and/or want a faster bike, a newer hybrid or road bike is fine.

Find some clear glasses.

Won't make that mistake anymore once 2-day prime brings me these beauties

Avante!

Beam pattern makes a big difference. I can see better with my 400 lumen light with special optic than with a higher lumen round/symmetrical reflector.

I use one of these on my chinese "1000 lumen" light. Not quite as good, but really helps put the light where you can use it.

By "full clip on fenders" do you mean something like the SKS seatpost mud guard?

SKS Quick Release Rear Fender

One of my favorite "accessories" on my bike.

I bike with a speaker all the time. I don't think it's a dick move (unlike jerks on public transit with speakers...)

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Been very happy with this purchase: https://www.amazon.com/gp/product/B01MTK45ZO/ref=ppx_yo_dt_b_search_asin_title?ie=UTF8&psc=1

I got one of these cthulhu face masks for warmth and ain't been messed with since.

Bleaugh. Would a summer balaclava help at all?

The Kryptonite Standard 2 is not going to be cut easily with bolt cutters. Proper locking technique will go a much longer way to bike security than lock upgrades. Don't be this guy.

Bike thieves are largely opportunists. Good locking technique, securing both wheels, and using a decent u lock should prevent 99% of issues. You can't prevent 100%.

I found that the Standard 2 was sufficient for me, though I've switched to the Abus Mini 140, which is a bit tougher and only slightly more expensive.

In your situation, I would get the standard 2 + cable, or the Abus mini and a set of locking skewers if you wanted to upgrade.

Having a second u lock exclusively for home (double lock when at home, take one when out and about) is reasonable -- but probably not necessary. You could buy two Standards for less than one Faghettaboutit anyway.

Don't buy the Faghettaboutit without thinking about securing your wheels, too.

Get an inexpensive runner carpet to park the wet/salty bike on. Use a hand pump garden sprayer out in the alley on the weekend.

Cheap over-the-ear headphones achieve a similar effect. I find that more sound leaks in through those than through my earbuds, and the headphones actually reduce wind noise (more aerodynamic than all the folds and bumps in my ears).

My "cans": https://www.amazon.com/SoundBot-SB240-Bluetooth-Streaming-HandsFree/dp/B00LJP9JRK/

Here is the mobile version of your link

Not true

Or you can spend $42 and get the one with the cable too.

I use one of these, usually on medium, which would be about 500 or 600 lumens, and aim it about 15-20ft ahead of the bike. It's got a tight beam pattern, and doesn't blind other riders.

edit: most of what everyone else says is dead on. Please don't be that ass with the flasher (every headlight that I've ever looked at puts out maximum lumens on flashing mode, and will blind other riders.) Point them where you want to see in order to avoid obstacles - not at the sky or straight ahead. I have a long history of doing endurance mountain bike races, so if you ever want to discuss real lights for seeing in the dark (race speeds! AT NIGHT! IN THE WOODS!) Let me know.