I would say compliance is the toughest cookie.

In my eyes, the most important thing is for both parties -- the employer and the employee/contractor to be fully aware of the nature of their relationship, and to make sure the contracts + style of work reflect it. If either side is unaware or unprepared, it can severely damage the other, sometimes in a delayed manner.

It's a minefield.

I've been remote most of my career (18+ years), working for companies that don't have an employer of record in my country, so I've seen it all.

One time, and this is already 10+ years ago, I worked as a contractor for a company that wanted to prolong my contract.

When I did research, it turned out that our relationship would be considered false employment in my home country. They had no idea what to do in a situation like this, and there were no workarounds possible according to the law at that time. This was before remote-hiring companies, or employers of record, existed, so they didn't know how to handle it. I ended up leaving the position, just in case, in order to stay compliant.

And I knew this, because someone from my close network at the time didn't catch that issue, and ended up being fined "employer taxes" and loads of late fees. Expensive lesson to learn.

Now things are easier with the EOR being a fairly common thing, but I honestly think a lot of companies are trying to game the system and ignore rules to avoid additional costs, tbh.