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I knew a guy named Jakov. His wife's name was Jillin.

I can give you my answer and even if OP answers you'll have two different perspectives. Because it's different for everyone depending on your lifestyle. I've been doing what OP is doing for almost 10 years now.

The short answer is for developing countries you'll need about $1,000 p/m and in Western countries everywhere from $2,000 to $3,000 depending on the country. That includes rent, food, insurance, Internet and transportation and a little bit of spending money. If you're a big spender then add more. You could also make it on half that, but then you just have the bare necessities and it's really hard to keep working when you're sharing a room with 6 others and living out of your backpack. You will also need to save extra for your traveling but what's common with a lot of these working travelers is not to plan ahead too much and let your traveling depend on how much you are able to save. I would recommend not planning ahead too much anyways because you never know when you arrive somewhere and make friends or start a relationship and decide you want to stay longer.

The cheaper countries where I've been were in South America and Southeast Asia which are popular destinations for travelers who work online because it's relatively safe, the facilities are pretty decent and more importantly you have fast and reliable Internet which is a luxury in most countries but a necessity if you're doing this work. It's normal in some places for the Internet to be down for days during a hurricane or cyclone or during monsoon season.

Rent is about $800 to $1,500 in the West and $300 to $800 in other countries. That's for a furnished apartment or home which is where I tend to stay. Of course you can stay in a hostel for a lot less, but that also means paying for an Internet cafe or office space to work, eating out every day, paying for a laundromat, etc. When you have a furnished apartment you get an Internet connection and you're done. One advantage a hostel has is that you meet other people there, while having your own place means you are on your own. I still prefer that because it means I can work at home quietly and I have no problem going out to meet people.

Besides rent and food you also need insurance. Which one you get depends on how long you'll be traveling but for the first year you can get an annual backpackers insurance for about $100 p/m. That includes everything you need like theft, damage, medical, etc.

Wherever I go I stay in large cities because you have all the facilities you need there, it's easier to meet new people, and there is (mostly) good public transportation. I use public transportation and taxis because it would be a hassle to buy and sell a car each time I arrive and leave somewhere. For the few times I go on a road trip I'll rent a car for a day.

I don't see it as overestimating but you clearly have a different lifestyle. Like I said you could get by with half of what I spend and that sounds about what you're talking about. And for someone with a limited budget and traveling for a short period of time that would be fine. But I couldn't see myself living in hostels for all these years.

I like to travel but I also like to have some luxury. I have a home with privacy, an office where I can work and I can invite friends over. That's different than what you're talking about. But it's good to get different opinions because there are a lot of different types of travelers. I also have friends with the same lifestyle who spend way more than I do.