passion is an important part of it, i think almost every obstacle can be eventually overcome if you have the reason to do so
personally if i owned a CarThing, enjoyed using it, and knew it was going to be EOL'd, i would try my best to keep it from becoming e-waste
documenting it makes it even better, since then everyone can share in your passion
Pretty much, yes. And knowing about common exploit strategies (the crypto engine partial overwrite for example is a classic one).
You start by reproducing exactly what other folks did. Once you've done that a bunch of times, you unlock 2 skills:
* The ability to handle simple situations that do not require deviating too much from what you've seen in the past
* The ability to learn new techniques simply by reading about them, allowing you to learn much faster
Apply those 2 skills for a couple years (which is not hard at all if you are genuinely attracted to this area) and you are an expert.
What is marvelous is that you don't need to know about those steps, you just follow them naturally when you are passionate about something.