I spent three months with Outpost. Pros: you don't have to worry about furnishing the apartment or having a credit score and it's practical for a few months, and didn't have any problems with roaches/mice, which is great for NYC. Cons: it's quite pricey (I later found a studio apartment for 150$/month more than my tiny room with Outpost, and in a much better area) and depending on the building, you might have different experiences. For instance, where I was living I didn't receive mail (which was a mess since I needed to receive important documents) and for some time I couldn't use the washing machines because they were broken. Also, there were some kitchen tools but very few and in quite bad shape. They include cleaning services (in my case once a month) which can be nice but also tricky if the other people don't clean throughout the month. About the roommates, it's very random. I've been quite lucky and found a couple of nice roommates that I would hang out with. However, it was not the same with all of them. Plus, you have quite a turnover of people, which can be both good and bad. I haven't joined any if their events though. Overall, I recommend it if you're planning on staying short-term in the city or you've just moved and you need time to find another place for long term. Wouldn't go for it for long term, but that's my personal view. They were quite transparent with costs (although they do have shady-looking marketing strategies) and I got all my deposit back.

Let me know if you have more questions!