Look beyond the borders. Have you thought about disappearing to Europe? Or if remote work is critical check out https://nodesk.co I worked as an engineer for a startup in san Fransisco while travelling around South America for a year, was amazing. Source: 9 months ago

Hi all, how long and how much would it cost to build a similar site? https://nodesk.co. Source: almost 2 years ago

NODESK is a fantastic resource for anyone looking to learn more about getting into the digital nomad/remote work game. Not just a remote jobs board, this site features a vast collection of articles and tips written for, by, and about taking on this exciting new lifestyle (hint: you may even find some great deals on travel gear)! The remote jobs board section of the site is no-frills and straightforward, and broken... - Source: dev.to / about 2 years ago

NoDesk helps you find remote jobs and connect with companies that offer you the freedom to work remotely from home or places around the world. Every remote job is hand-picked, tagged, and organized to help you find the perfect opportunity. - Source: dev.to / almost 3 years ago

Nodesk.co is great for a variety of different industries, and I have a couple of friends in similar situations as you that found decent jobs based on their retail experience. Source: almost 3 years ago

Might want to check out taxjar.com, I haven't used it but one thing they claim to do is help with this compliance. Source: almost 2 years ago