Remember this is a company that already has a major international business in one of the most regulation industries. Adding in a few real-estate deals is unlikely to be a major source of friction.
This article (https://www.curbed.com/2019/3/26/18280774/wework-real-estate...) seems to indicate that big corporate clients are quite happy to do exactly what I described. I suspect this probably also has to do with transferring CapEx to OpEx.
Perhaps Stripe, specifically, thinks they have a better bead on this than employing someone like WeWork.
Of course, but I assume that WeWork offered them a better deal.
It's the same as a individuals buy vs. rent scenario for a house. Sure, rent may be cheaper, but there are long term pros just holding the property yourself if you can afford it.