Personally, as a freelancer/consultant, I never think there is a right time for anything in my life. Of course, you might feel differently (and it probably is different). I'm offering advice from my perspective only, and I don't have a home to make, or children to worry about. I've been freelance/consulting/whatever for about 2 years, so make of this what you will, but I'm still early stages having just been where yo…
FWIW, I futzed with Upwork years ago. It became super clear that it wasn't where I could sell my skills (deep backend, sre) effectively and come out with outcomes good for me and the client. I do FTE work but occasionally dream of the side income (less so these days ha). :)
I see the control over my time freelancing affords as my ticket to eventually make living off my own products (some day ;)