Getting Started
Everyone's journey will be different, but here are some resources and intermediate steps I've found useful on the way to relying on (e)cycling more.

Testing the bike waters

Bike Shares

I citibiked in NYC and JC for years. I loved it and still love it. Electric-citibike inventory is hitting critical mass, and the system is expanding all the time. I will always keep an annual Citibike membership on auto-renew ($179, or less than 2x a monthly MetroCard; still a great value).
There's also an explosion of scooter-shares, moped-shares, on-demand e-bike leasing services, etc. In my experience, most such things are worth signing up for and trying to use a few times, or for a few months, to see how they can fit in to your life.
I "graduated" to owning a bike somewhat accidentally; my local ferry shut down during COVID and I needed to get to a ferry stop in Hoboken (outside the Citibike JC area at the time… no longer!). I'd also started to want to do longer rides, and felt constrained by the Citibike network limits.

Renting

When I started researching buying bikes, I rented a few bikes from my local Grove Street Cycles. One afternoon on a modest "hybrid" convinced me that, though I love Citibike, I'd outgrown it more than I realized, and a whole new class of mobility and freedom awaited from owning (vs. renting ≀45mins at a time) a nicer/lighter/faster bike.
I definitely recommend seeing if you can rent a few different kinds of bikes – including e-bikes! – as a way of learning about the options in a way that is more visceral than anything you can get reading reviews.

Safety

A few specific safety sub-topics:

Stats

Bicyclists killed or seriously injured (KSI), total and per 1e7 trips, over time; total is roughly flat around 350/yr, rate drops from 80 per 10MM trips in 2000 to 10 in 2018
    Bicyclists killed or seriously injured (KSI) is roughly flat since 2000 (around 350/yr)
    The rate (per 10MM trips) dropped from β‰ˆ80 in 2000 to β‰ˆ10 in 2018
In a 2014 analysis, incidence of cycling death took place at a mean rate of 4.7 deaths per 100 million kilometers cycled in the U.S., compared to 1.3 deaths per 100 million kilometers in Germany, 1.0 in the Netherlands, and 1.1 in Denmark.[6] In the United Kingdom, cyclists have half of the rate (killed and serious injury per km) of motorcyclists but eight times the rate for motorists.[7]​

Speed

Cities are often the safest places to cycle, because cars aren't going as fast:
Probability of pedestrian fatality, when hit by driver, as a function of driver speed: <10% at 30kph, 80% at 50kph, β‰ˆ100% at 70kph
Biking is often safer if you can match the speed of traffic, which is one reason I feel much safer on ebikes.

Fear

As I've ridden longer, and as cycling infra has improved around me, I less frequently run into situations that scare me or spike my blood pressure. I've become more deferential to pedestrians and the letter of the prevailing traffic laws. The whole cycling experience has become de-adrenalized a bit.
That's allowed me to notice that fear is consistently the reason that I make mistakes, break traffic laws, etc. A driver will do something scary, or I will find myself extremely vulnerable on a road designed for cars, and my priorities shift. I generally don't fault vulnerable road users prioritizing their safety.

Riding on sidewalks

Cyclists would rather be on roads than on sidewalks, but will always use sidewalks where roads are not safe.
The solution to sidewalk-riding nuisances is to make roads safe for cycling. Pedestrian/Cyclist conflicts are a distraction from cars' being allocated most public space.
​ ​
Comic showing drivers with plenty of space and pedestrians and cyclists fighting for scraps
comic showing roads full of cars and parking, a family on bikes on a sidewalk, and a driver saying "If you take this parking for a bike lane, where will I park my car?! You're not considering my needs!"

Stopping at stop signs + red lights

Cyclists should stop at stop signs and wait at red lights, but a 250lb cyclist+bike running a stop is very different than a driver doing so (in a 4000lb car with its own climate and sound system, and a 100mph top speed):
    A cyclist slowing (e.g. to yield to any pedestrians present) before rolling through a stop sign at 5mph has similar kinetic energy as a car rolling through a stop at 1mph.
    Cyclist also generally have better situational awareness than a driver, and more at stake (being more vulnerable in the event of a crash).
Several states have "Idaho stop" laws, which allow cyclists to treat stops as yields and lights as stops. These are great, not least of all because they emphasize yielding to pedestrians in a way that gets lost when cyclists have been overlooked (and asked to follow rules made for cars, by default).

Braking

​Sheldon Brown on front brakes is a good read; beginners are taught to be careful with the front brake (left hand), to avoid potentially going over the handlebars. As you get more comfortable riding, you should reincorporate the front brake for maximum stopping power.

Helmets

Image of a helmet-less cyclist riding next to a helmet-wearing motorist, with caption: "Β½ of all serious injuries happen inside motor vehicles – if you drive a car, wear a helmet!"

Lights

Lights are definitely useful for safety; "more" is "merrier" as far as I'm concerned.
Something I like about ebikes is that most of them have integrated lights. Not having to fuss with charging separate lights makes the whole process of riding safely at night much simpler.

Hi-Viz Clothing

rear GoPro view of me riding electric Brompton on 5th Ave in NYC
Drivers seem to mess with me less when I'm wearing hi-viz.
​This Amazon vest also lets you print custom images on it:
blue hi-viz vest with an image of Kermit standing one-legged on a bicycle seat

Route Planning

Street View

Google Maps Street View has been indispensable for checking out roads before riding them.
Ironically, it can even help identify when Google Maps directions are sending you somewhere unsafe, like this 4-lane, 50mph no-shoulder highway:
Screenshot of Street View showing the 4-lane, 50mph approach to a bridge on NY-22, a 50mph speed limit, and an SUV parked in the last few feet of shoulder before a bridge railing goes right up to the edge of the lane
Screenshot of the same road on Google Maps, showing a dotted green line along it and a legend that indicates it is a
I also used Street View extensively when making bit.ly/mellowbikewestchester (discussion below); after a while you can get pretty fast at warping ahead by many increments, zooming in to scan for speed limit signs, and using the map detail in the lower-left to teleport longer distances, but it gets a bit tedious after a while. An interface better tailored to this use case would help.
I've also been surprised not to find any decent map apps that make it easy to see roads' speed-limits at a glance. I suspect the required data may exist in OSM, but haven't had a chance to explore it much yet.

Ride with GPS

​ridewithgps.com is one of the best tools for planning/sharing/discovering bike routes.
Screenshot of a "Ride with GPS" route, showing a map view, elevation over distance, and summary statistics
Here is a route I made (and hope to ride soon) that includes 23 NYC bridges (all Manhattan bridges and a few in Brooklyn and Roosevelt/Randall's Islands) and 1 boat:
RideWithGPS screenshot showing route around Manhattan, zig-zagging back and forth over bridges

Strava

​Strava also has route-planning features that seem decent; here's the same "23 Bridges 1 Boat" route on Strava.
Both Strava and RideWithGPS make it easy to export and import things in GPX or other formats, so data portability is easy, which is refreshing.

"mellow bike maps"

Inspired by the Chicago "mellow bike map", I made a "mellow bike Westchester" Google map while staying up there for a few weeks and trying to plan rides (for myself and others less experienced, where it was extra important not to accidentally end up on no-shoulder 45mph roads):
Screenshot of Google map of greater Westchester County, NY, with streets color-coded by bike-friendliness

Traveling with E-bikes

Flying with Ebikes

This is mostly a non-starter as ebike batteries are generally larger than the FAA and commercial airlines' allowable limits.
​TSA says:
Lithium batteries with more than 100 watt hours
Carry On Bags: ❗️ Yes (Special Instructions)
Checked Bags: ❌ No
Lithium batteries with more than 100 watt hours may be allowed in carry-on bags with airline approval. One spare battery, not exceeding 300 watt hours, or two spare batteries, not exceeding 160 watt hours each, are permitted in carry-on bags. For more information, see the FAA regulations on batteries.
❗️ The final decision rests with the TSA officer on whether an item is allowed through the checkpoint.
I think the electric Brompton is within the limit here, as its battery is 300Wh, and the bike itself folds up small enough to fit in an overhead compartment (and can also be checked).
A folded Vektron can fit into a large checked bag, in principle, but I don't know of a way to fly with the 400Wh battery.
The VanMoof and Creo don't fold, and would basically have to be taken apart to be shipped, and their 504Wh and 320Wh internal batteries are too large to fly commercially.

Trains, Boats

Other modes are generally friendly to multi-modal travel that includes e-bikes:
    ​Amtrak's Bike FAQ says:
    Electric bicycles under 50 lbs. are allowed in checked baggage and on trains with walk-on bicycle service. Gas-powered motorized bicycles are prohibited.
    That means all my e-bikes should be allowed (the Vektron weighs in at 49lbs, without anything on it; with bags/etc. mine is in the mid/high 50's, but since it folds up I am optimistic it would be allowed)
    I frequently bring ebikes on the NY Waterway ferry (between NYC and NJ)
Electric Brompton inside a NY Waterway ferry from NJ to NYC
I've run in to a couple of grey areas:
Creo and Vado ebikes on a Metro North train
In general, some e-bike prohibitions seem aimed at heavier-duty (esp. throttle) e-bikes; my pedal-assist bikes generally look/weigh/fit similarly to regular bicycles, and get a pass.

Starter Packs

VanMoof X3 ($2300; $3k w/ "Peace of Mind" plan)

The VanMoof X3 is the cheapest of my 4 ebikes, but is the best all-around and my go-to e-bike for trips around greater NYC.
It starts at $2300, but I added:
    VanMoof's 3yr theft+maintenance plan ($590);
    ​front basket ($89), back rack ($69)
    ​fleece-lined pogies ($47) for toasty hands in below-freezing temps (I've only had it during winter months, so far)
    ​bungee cable set ($14) for securing items in the front basket
    ​Extra battery ($350)
      Still waiting on delivery, have not needed it that badly
      Excited to be able to go on longer rides (it should extend my range, using liberal boost, from β‰ˆ30mi to β‰ˆ50mi)
This $3k-$4k package should let you replace/improve a wide class of trips that you'd otherwise use other modes for. See more discussion here. Also, the bike + plan can be financed for $83/mo.

​RadPower: <$2k

RadPower are a popular brand that is aggressively targeting a lower-pricepoint, mainstream audience. My 5th/next e-bike will likely be a RadWagon; they seem to be easy to order online and shipping reasonably quickly.

Reading

This was consistently one of the highest-quality review sites I saw. I learned to seek them out on a Google results page, or go there directly to search for a specific bike.
They did the best job of showing critical stats about bikes in an easy-to-scan format, especially including stats that the industry is sheepish and user-hostile about (*ahem* bike weight *ahem*).
Here's are their reviews of a Creo similar to mine and my Tern Vektron Q9. Their brand pages are great too: the Specialized reviews page was very useful in sorting through a bunch of confusingly-named models.

​r/ebikes​

Nice forum with encouraging/inspirational stories and examples
Vendor-specific subreddits are often, e.g. r/vanmoof or r/brompton.
Last modified 2mo ago