I began using Tailwind in January 2019 to try to boost the traffic to my website from Pinterest. It's definitely achieved this for me and my resulting mailing list signups are growing. I suspect I could be getting even more value from my subscription if I pinned more often and made better use of Tailwind Tribes. I do believe it's worth the expenditure though. I haven't used the Instagram functionality of Tailwind.
I feel some of the analytics are over-inflated, for example, measuring potential reach, rather than the number of people you actually reached. I'd like a more comprehensive way of knowing if Tribes are getting worthwhile results for me, too.
Anyone who's hoping to drive traffic to their website through consistent Pinterest use, but doesn't want to spend time pinning every day. Will probably work better if your target audience is female and interested in lifestyle/food/travel/blogging topics.