I actually used to work with the original founder of the freelance writers den, Carol Tice, before she sold it. This was almost 8 years ago now though so things may have changed significantly since then - I have no affiliation with them or incentive to promote them now, this is just what I remember hearing from various community members. The biggest appeal back then was the job board, it was more tailored and exclusive, like many paid job boards, and I believe there were also some connections with various publications/employers that might get you a better chance of getting gigs with them. I have no idea if the job board is of the same quality now (or if it still exists even), but it was pretty solid back then. Of course there was training and other such stuff, but like you said in other comments most of that could be learned online - Carol has also published several books where I'm sure you could learn the same stuff. The other big appeal was the community, one advantage I can see to paid communities is filtering out the junk. Everyone who's paying to be a part of a community like that is more serious, versus the low effort/mediocre posts you see frequently on free places like this (and this is one of the better spaces). Again, can't speak to the quality now, or even if all of those aspects still exist, but those were the two big selling points I remember talking to the members about. I'm sure there was other stuff too, but honestly this was so long ago I can't remember so take this all with an appropriately sized grain of salt. Answer from InconspicuousBrand on reddit.com