This actually seems like several questions!
Quality is still the name of the game. There have always been writers in the world who've risen above the rest, and others who've sunk to the bottom. The only thing that's changed in this century is the ease of accessing information.
Sturgeon's Law posits that 90% of everything is crap. Spend twenty minutes on YouTube and you'll find this to be true. The average person has become extremely good at recognizing poorly-written material, whether it's a blog post or a motion picture. The biggest challenge for an individual writer today is the struggle to improve and focus their craft.
Even with piracy running rampant on the internet, the good stuff tends to filter to the top while anything less than excellent falls to the wayside. This might come down to networking and right place/right time luck, but I think this is generally true.
We live in amazing times. There has never been a period in human history where so many smart, literate, talented people were connected together. The challenge for the modern writer will be differentiating him/herself from the pack. In that regard, the future of the modern freelance writer will only be bright if they are willing to take the time to market themselves and their work.