Hiring teams that are just "getting their feet wet" with remote workers are going to be more hesitant. When there is an in-company precedent for what remote work is like, I find them to be more open.

For me, making the transition from on-site to remote work was difficult. Like any job skill, it's something I had to be able to demonstrate proficiency and/or history with before I could land full-time, remote employment exactly where I wanted.