Our onboarding materials explicitly say, "NYC is not HQ". And it's not HQ. It is just an office we leased because we ended up with 10+ staff in NYC and they preferred an office to a co-working space, for security/privacy. (If you've ever lived in NYC, you know it can be challenging to have a home office at any reasonable cost, due to typical square footage of living spaces. That's part of the reason I left NYC.)
We are a Delaware C-Corp. Yes, we have our mail sent to NYC, but that's for the lawyers/accountants.
As for the NYC staff, they find that one "problem" with the office is that it has a "library atmosphere". I personally don't think that's problem, but I am the CTO and an engineer, so I prefer quiet & focus. Some people expect an office to have "energy" and ours is definitely lower on that scale. I try to remind people that "the web is our office and the front door to that office is your internet connection."
Are people happier in our NYC office than on our remote team? Hard to tell, but the NYC folks complain about commuting a whole lot, and often take the occasional work from home day to spare themselves of it. I never hear those complaints from the other staff. I guess one benefit of the NYC staff is that they can have happy hours and dinner/drink outings, which inspires some jealousy on the non-NYC team.
We make up for that by throwing annual and semi-annual team retreats. Our last two were in Upstate NY at a writer's retreat campsite (really fun getting to know everyone over campfires and s'mores) and the one before that was in Reykjavik, Iceland, where we rented out a whole hotel and got to know each other on city and countryside excursions during 23 hours of daylight!
Where on the startup journey does transition to distributed make sense? Well, for us, day one worked! We reversed the typical evolution. We were 100% office-free for a few years. Then, in 2012-2013 or so, we got an NYC office, after a frustrating experience with a sub-leased co-working space for the NY staff. But we refer to it as the NYC internet cafe, not HQ. I think that is healthy for teams like ours.
Are distributed teams more likely to outsource stuff? I dunno, probably. We outsource commodity accounting/legal/payroll/benefits services, but we have an in-house finance/collections team. We also outsource PR, cloud hosting (obviously), and we use a lot of SaaS services.