As a "forever globbetrotting" remote worker, I wanted to share some thoughts about it with you.
First thing first: do NOT ask yourself what a company can do for you (remote ok or not), showcase yourself and what YOU can do for a company. Here is what I mean: I've been working two years in a company which is definitely not remote friendly. I wasn't even thinking about working remotely, but life is full of surprises. I'm now (remote) fullstack lead developer of that exact same company, having 2 offices with developers spread over the world. I participate meetings, answer my phone line as if I were with all of them. We all admit I'm way more productive at work, some (including my boss) saying I may be paying an Asian guy to be "answering every time they need me". It's not about convincing each historical company to be remote friendly, it's about these companies fit the market (as they always do to keep on making money) if they want to keep on hiring most talented professionals!
If you know your stuff, you are the lucky guy. Find the job YOU love, and find it where it is. Convince them you are the guy, be opened to spend one or two weeks with your team few times per year, wherever it is, and be clear that your teammates timezone is the one (yes, you may have to be online for a meeting at the middle of the night, but the week-end after while your colleagues will be somewhere fun not that far, you will be at Niagara Falls, visiting Dubai, or sailing a lagoon in the Indian Ocean). Then just do it, you will rock it, both of you being happy with it. And do not fear realizing you work better in an office with teammates.
Having to keep a budget while travelling, I would definitely NOT recommend to be freelancer without some recurring work from multiple well-known clients (who really pays). This is NOT something to treat lightly. No money: nothing good for you, and your family. Clients do NOT contact you just because you say you are good and your website is awesome (I've been running two companies for 10 years before, I promise I know my stuff). Consider it thoroughly with your wife, even if she makes enough money for the whole family. Many (but not all) freelancer testimonies are fakes or pure dreams, it's not rare digging around you will find them always staying in Asia because it's inexpensive and they do not make enough money to get elsewhere!
Last words, regarding freelancer stuff or nomadism, keep in mind this is getting huge nowadays, and becoming a business for a lot of people who just think about making money from you with fancy website you may need (or not). I'm pretty sure you will easily find links (if not some on this thread already). Just be conscious about what it really helps you to. Having "a community" to answer questions is free as you can see ;)
In a train from Aveiro to Porto, Portugal, I wish you fame and fortune for your career! But fortune may be enough ;)