No Stupid Questions

Not technically an American but lived in America for a long time, also not eligible to claim citizenship anywhere. I hope I'd be somewhat qualified to speak on this

There really aren't that many countries which are a step up for an American IMO. Probably a good number of the EU/EEA countries, places like Canada/Australia/NZ, and mayyybe places like Singapore and a few more... Fewer if you have a strict limit on English, in that case maybe only places like UK & the Nordic countries; maybe also the Netherlands, but I've heard mixed information about language requirements there. This is a pretty short list, so I think you could probably have a passing knowledge of all of their basic immigration processes without spending that much time on it. But yeah you are right, for any expat/immigrant wannabe it usually goes like this:

Winning the "life lottery" (ancestry, asylum, or a literal lottery like the US) -> "Buying" your way in via Golden visa -> Love knows no borders so marriage -> Workers visa, aka getting sponsored to work

The first three obviously don't apply to you or me TBH, so work sponsorship it is: either international transfer via a large international company (does that happen often for trades people?), or finding a job in your target country. I think others have mentioned this, but since you will likely be immigrating via work, secure a job first. Don't even think about anything else without a solid job offer. I didn't follow this advice myself and literally got screwed; I spent several hours learning German everyday during a really busy time of my life, wrecked my mental health along the way due to stress, and never ended up finding a job in Germany in the end... Don't be like past me

tradesman with a lot of technical skills with some specialized skills in short supply

Probably your biggest asset. Some countries like Canada and Australia/NZ publish their skill shortages, so if your skills are on them you'd be in very good luck. There are subreddits and discussion groups on these topics so I'd look into them

Note that in Australia, allegedly the real job shortage can be quite different from the published list. This doesn't hurt your chances of moving there per-se, but can make your life difficult after moving in, especially if you don't have a large amount of savings

Also, I'm not sure exactly what trades you are in (for the sake of privacy I prefer not to ask), but different countries may have different regulations. It is possible that you may not be allowed to work in the EU without local certifications for example. I don't think it is an impasse per-se, but I'd definitely investigate this beforehand

But anyways, if you are interested why not try and apply for a few jobs first? You never know :D

Neither of us is very good at picking up a new language (lord how I’ve tried)

To be honest... that doesn't sound very good. Comes without saying that most places expect workers to speak fluently or at least B1 in their native language (which is also required for immigration purposes for most countries), and the English-friendly places (such as Ireland) can have extremely high demand, which can cause other societal complications

I am taking what you said at face value, since I have seen first-hand how much my boss (German) struggled with learning French and had to settle for learning Dutch instead lol. Nevertheless, for most people it isn't that hard to at least get a passing conversation skill level in a target language in a few years especially with full immersion & government/employer-sponsored language classes, so I wouldn't completely rule it out just yet! If you're able to deal with other languages, there are lots of EU countries that have plenty of opportunities; maybe even some more developed parts of Africa would do as well