Source: did my undergrad in US, spent 5 miserable years on H1B tied to a single employer who kept delaying my PR application, because of which I couldn't travel freely internationally. Moved to Canada, finished my Masters, got my PR in 6 months. Now I can travel whereever I want. Thanks, Trudeau!
Nothing is easy, especially when it comes to moving countries.
I can offer insight on the Netherlands specifically. Other EU countries might have similar systems in place, though each is different.
There are generally three options for an American to move to the Netherlands for work:
1) get a highly-skilled job outright with a Dutch company that fulfills certain criteria in a position which cannot be filled locally. Not all companies are eligible to hire highly-skilled migrants from abroad (they have to apply to do so, and there are considerable costs involved). There are some nice tax perks to this (see 30% ruling).
2) start your own business with relatively small investment capital (<5000eur) and gain residence through the Dutch-American Friendship Treaty (https://en.wikipedia.org/wiki/DAFT)
3) get a Master's degree from a Dutch university, after which you'll have full access to the Dutch job market for one year, then you'll receive a highly-skilled migrant work visa
The above provide a path to a renewable residence permit for highly-skilled migrants. Typically you'll start working with a temporary 1-yr contract which, assuming things go well, will be extended for another year. After 2 years of temporary contracts and if the company still wants to keep you they'll give you an indefinite contract. After this, you'll next receive a highly-skilled migrant visa valid for 5 years.
An American is eligible for permanent residence after having lived uninteruppted in the Netherlands for 5 years and after passing an integration test. The integration test requires that you speak Dutch, though honestly this is not so difficult (it's at an A1 level and the tests are fairly basic; they also test your ability to function in the Dutch job market and society which is a bit silly to ask of a highly-skilled migrant who's already successfully lived there for 5 years).
I'm sort of in the process of gaining permanent residence. I have the time, the degree, the job, and most of the Dutch; it's only a matter of passing the test and submitting the paperwork. But since I have a 5-yr permit and permanent job contract already I'm not in a major rush.
edit: I feel like it's important to point out that the highly-skilled migrant permit is obtained for you on behalf of your employer, however it is not tied to that employer. You're free to find other work elsewhere without any retribution.
My holiday work visa ran out and I switched to an Essential Skills visa. I wish I had ticked the other box and gotten "Work to Residence." It cost more but you get a residence without travel restrictions after a few years. You can also apply for a full resident (a few thousand dollars) visa and you become a resident, but with travel restrictions. If you leave for more than six months, you lose it. If you stay past a certain point (I think it was 2 years or something like that), you can apply for a permanent resident without travel restrictions.
The US doesn't have the concept of "Resident without travel restrictions." If a customs agent asks you questions and thinks you don't actually live in the US (e.g. you only visit once a year), you can potentially lose that green card. It's arbitrary though, because the US is only of the only countries that doesn't do a customs check on exit (it's impossible to determine if someone overstays in America, unlike every other developed country in the world).
For most countries, to immigrate you must be on their essential skills list. I've considered getting another Australian visa (I lived there too; holiday work visa only), and the process involves putting in a letter of intent. If you're selected, you can apply. The fees are steep (usually a few thousand dollars), but if you're selected, you get residence and a window which you must arrive by. After a few years of holding a job or being able to support yourself in your field, you can apply for permanent residence.
Immigration without an essential skill is extremely difficult, for all countries. This is a stark contrast to immigration only a few decades ago, when countries like the US and Australia were in desperate need of all types of workers.
* actually you might have to pay to get some translations certified, or if you want a lawyer.
I even know 2 Americans citizen who have a long term self employed permit.
One detail: you can travel all over the Schengen Zone for tourism, but you still can work only in one country.
Didn't seem at all hard to get to work there. Don't know about permanent residency, though.