Indeed, especially here in Asia where the cost for a Western standard of living is comparatively very low. I've also been self-employed overseas for years and would never go back.
One quick bit of advice, get out of the hostel mentality now! You're not going to be crashing at a different place every night. You should be looking for accommodations that rent by the month. You can get a decent studio apartment across the street from where I live in Thailand for about $150 /mo. WiFi there is shared amongst all the residents of the building so that can be inconvenient. My 2bd, 1ba, full kitchen "duplex" costs me $230 /mo. My 14/1Mbit ADSL is $30 /mo. I started with a 6 month lease contract but could have probably got the place with no contract if I had pressed. Also, housing contracts here aren't worth the paper they are written on. If you don't leave much of a deposit or if you use it for your last months rent, a very common tactic here, you cave hardly any liability and can move anytime you want. The OP should consider themselves as a part-time resident, not a traveler, and should be looking for accommodations to match.
3G isn't everywhere in Asia yet but it is in most major cities and is expanding very rapidly. In some countries it's very well deployed. It's fast enough for work and besides cell/mobile phone tethering you can buy an "aircard" that accesses the GSM network. Then all you have to do is buy a sim card and sign up for a monthly data plan for whatever country you're in.
I've got a Kali VM and travel with a wifi nic that can run in monitor mode and do packet injection so I rarely have a problem finding an internet connection anywhere I need one these days, even when hard pressed to find a good open one. I'm a very courteous uninvited guest though, I don't mess with others' network configs nor saturate their bandwidth.
Sign up for Couch Surfing https://www.couchsurfing.org/ no so much for finding people's couches to crash on but for networking in the new country you have arrived. The expats who already live in the countries you are coming to will be more willing to help show you the ropes and how to get up on your feet in just about any country you land. Think of it as an easy way to make friends abroad that will help you integrate into the new community you're in. For example, I found out about where I live by word of mouth, it was not advertised, and that is the kind of thing people who already live where you are going can help you with.
And finally, yes, here in Asia all major malls have wifi and internet cafes or Starbucks and they will let you sit there all day long for purchasing a $3 cup of coffee and/or a $3 pastry. Don't look for public libraries here though, you won't find many / any.
Just do it and don't look back. Don't let the neckbeards here who haven't left their crypts for a month get you down. You'll have the time of your life and, if nothing else, the value of the experience itself will be immeasurable. Send me a PM / email if you want more specifics about how I made it work.