I did a lot of freelancing in graphic design before I started limiting it to editing and writing. But I subcontracted to someone I trusted a lot, and she paid on-time and fairly. It depends on who you’re contracting with. Most of the time, though, it’s with people you don’t know and will never meet, or worse, big corporations. But oddly one of my best gigs was with a very large and well-known company in Germany and they were delightful to work with, paid a higher hourly rate, and promptly.
Then I did editing and writing for an old friend of mine who was The Editor for a large group that put out two trade journals from NYC. Cool stuff, right? The people in NYC were AWFUL about paying me, and wouldn’t pay me through Paypal or direct to my bank, but would mail me, god forbid, a damn check. Which would take 7 full days to move by regular mail from NY to Denver. This went on for 6 years. Even though I had my name on the masthead of two glossy magazines, and learned AP style and how to write good headlines, it was a PITA.
Would I do freelance again? Boy, it really depends. I would thoroughly vet whoever before I said yes. And I would set out my own terms from the start, and no checks and USPS, thank you very much!