In my experience, legal and tax complexities are more than sufficient to restrict the countries that we have remote workers living in.

We work globally so practical things like timezones aren't really a factor; we have plenty of experience working around them. That even goes as far as things like personal security in locations that are particularly dangerous. In my line of work that usually means risk of kidnapping. It will be a factor we take into account but wouldn't usually be decisive.

Having said that, I have been involved in setting up multiple offices in new locations. But only where we're expecting to have a significant presence over the long term. Essentially, where we can amortise the costs of legal and tax expertise.

Source: reasonably senior executive at a very large, global financial organisation.

My company hires remote staff worldwide. We use Deel and Remote and normally include time zone rather than location if it's relevant. There are countries where we don't hire for geopolitical reasons like China. Having staff in those locations can make it complicated if you seek funding (including loans).

Having said this most companies I encounter that have overseas workforces set up local corporations where staff work in proper offices. We have a lot of customers so I see this a lot.

If you want to work remote, then easiest approach is to establish yourself as a company / self employed and do effectively freelancing. Entering into employment contract with somebody outside your legal presence is a problem for lawyers. Paying an invoice to a company somewhere in Eastern Europe is not a big deal.

A major factor for many companies is the strength of intellectual property rights and their enforcement. For most tech companies, their IP forms one of their primary moats, so naturally, it follows that they will be adverse to sharing their IP with anyone who is not within a jurisdiction that would honor the contract that outlines those IP rights. Many jurisdictions have IP laws on the books, but they are scarce enforced, making them effectively useless. And even those with relatively decent IP laws, litigating such a matter in a foreign land is not worthwhile for many companies. If it was simply a matter of cost, more companies would willingly engage qualified engineers all over the world, but given the risk of IP compromise or loss, that bargain ends up looking penny wise but pound foolish.

legal entities cost millions to set up for big companies

many companies are afraid of the employment laws they don't fully understand

timezones/cultural differences

There are still contracts for working remotely at companies like this, but you've gotta be known for solving painful problems that they can't fix themselves

One thing I learnt eventually is: it's not a good idea do business with any party that would be impractical to sue if need be.

Meeting times and already existing taxation systems set up in those countries.

Synchronizing meeting schedules is one main reason.

yes, it's all of the above.

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