Addis Ababa

I'm editing my original review given how Addis has changed in the past year:

If you don't like chaotic developing world cities and don't want to be exposed to issues like petty crime, poverty, etc. - stop here, you won't like Addis one bit.

If you clicked here because you're a seasoned traveler coming in with eyes wide open that Ethiopia is (very) poor but the experience and empathy to make it work in order to have an amazing travel experience: you can make it work. Ethiopia is the most foreign experience I have ever felt coming from a Western perspective. Nonetheless there are still loads of cafes, food is amazing (though you will get sick at least once), weather is good, everyday life is cheap. It's enough to give you a home base to explore other areas of the country (which are insane travel experiences), and there is a young professional/expat scene to engage with when the rest of the city is overbearing.

The flip side is: the culture can be a bit inscrutable and not particularly concerned with being hospitable to foreigners, the entire city is under constant construction trying to turn itself into Dubai, and the infrastructure lags - internet is slow, foreign apps don't work (local business regulations are onerous), and the new apartments sit empty because the prices are exorbitant. On top of that, the security issues in the rest of the country affect the vibe a lot, so it's tough to plan going there, but if that ever turns a corner I would recommend it for (very) adventurous travelers because the payoff in terms of experience is there.

I have friends here, so I will be a regular visitor in conjunction with leisure trips further afield in Ethiopia, but not sure I could hack more than a few weeks at a time.

If you don't like chaotic developing world cities and don't want to be exposed to issues like petty crime, poverty, etc. - stop here, you won't like Addis one bit.
If you clicked here because you're a seasoned traveler coming in with eyes wide open that Ethiopia is (very) poor but the experience and empathy to make it work in order to have an amazing travel experience: you can make it work. Ethiopia is the most foreign experience I have ever felt coming from a Western perspective. Nonetheless there are still loads of cafes, food is amazing (though you will get sick at least once), I was getting 25mbps on my phone, weather is good, everyday life is cheap. Modern apartment blocks are going up like crazy, but from a low base so housing can still be relatively expensive for what you get. It's enough to give you a home base to explore other areas of the country (which are insane travel experiences), and there is a young professional/expat scene to engage with when the rest of the city is overbearing. Granted, I spent only a week in Addis but have made good friends with a small group of locals/expats who had good insights, and have spent several years in Africa.
The security issues in the rest of the country affect the vibe a lot, so it's tough to plan going there, but if that gets resolved I would recommend it for (very) adventurous travelers because the payoff in terms of experience is there.