Thanks for your thoughtful intro, Andy! Welcome to Nomad Forum!
First off, those are some great goals for digital nomadism. I've had some life-goals to study Korean and Japanese, and for the last 10 years I was letting those dreams evaporate as I explored my career options in America. Now that I'm in Thailand and the possibility of working feels a little more real, so do those life goals. They still feel quite far away though, which brings me to one of your questions:
Is it more difficult becoming a digital nomad when your skill set is not in creation ?
Honestly: yes. It's even difficult being a digital nomad when my skill set is in development. Here's my story so far. I've done web development for about 4 years now. Before I left my last job, I felt like companies were knocking down my door trying to recruit me. I don't think I'm being modest in saying I'm nowhere near the top 1% of developers out there, it's just a hot market. For instance, companies were eager to fly me to different parts of the US for an on-site interview after a pretty simple screening that any competent developer could pass with 1 year of experience. Once I expressed interest in working remotely +/- 12 timezones, a lot of that employer-excitement dried up.
Being a digital nomad is taking a communication sacrifice for me and my potential clients/employers. I'm originally from the states, so there's a large time-zone difference between there and Thailand. The timezone difference literally couldn't be larger; it'd start to shrink if I travel in either direction. That may be different for you, depending on where you want to travel, but I didn't factor this in enough before moving.
I am moving forward with my goals: I'm learning more about self-managing my time and financial runway, I've secured my living situation for the next 6 months, and I do have potential full time and contract work in the pipeline. I don't regret the decisions I've made, though I will say that financially I've gone beyond what my pessimistic projections were for securing remote work. If I could say one thing to my younger self, it's that when it comes to nomad-friendly work, a bird in the hand is worth two in the bush.
I've sent you a personal message on Slack in case you have anything more you'd want to discuss. Wish you the best of luck!