OP

Part time, or “casual” job, in one of the most expensive cities on the planet, with no visa (presumably since you don’t mention it), that pays enough to cover your significant expenses and still have money to travel around too?

Good luck.

should I only date when I know where I want to settle down?

This seems obvious to me? I mean, casual dating knowing that it’s nothing serious sure, but you can’t even contemplate anything serious if you know that in X months/years time you’re gonna want to move away. You may find someone that would come with you, but if you’re dating a local they are likely to want to stay where they are…

Why is labelling you as American “putting you in a box”?

As another commenter said, Americans spend so much time talking about who they are, identities in terms of race, perceived heritage, etc… but to the rest of the world you’re just American.

But, why is that a problem? You come from America and have an American accent, so what do you expect people to assume you are?

But I assure you, no one cares about this perceived identity as much as you apparently do.

Agreed with the rest, you must speak Italian. But I don’t think this is really a strange thing, I mean it is Italy, you can’t expect any host country to make the effort with you in English and you not do the same.

I disagree that the bureaucracy is terrible, this to me feels like a stereotype that was once true and now just gets repeated by people who haven’t had to do anything official recently.

It can be slower than elsewhere, yes (although faster than France!), but in the last couple of years there’s been a massive digitisation of services and a lot of things can now be done online.

Even the things you need to do in person, in my personal experience, were painless (getting the electronic ID card, registering with the comune, converting drivers licence, etc)

Life in general, if you have a decent job you can live pretty well. Getting said decent job can be hard, but if you have some experience in your sector, speak the language play English, good jobs can be found. It’s shit for new graduates, which is why young Italians leave, but once you’ve got experience or skills to sell, it’s not bad. As with everywhere, depends on your sector, role, and qualifications.

Milan is a very “non-Italian” city, it’s pretty bland compared to elsewhere. It’s also very expensive, and cold in winter. Unfortunately that’s where a good percentage of the jobs are (but that doesn’t meant you can’t find something elsewhere, I’m in Rome)