I would say, in aggregate, I miss my favorite software remaining independent and/or not acquired (and then promptly shut down) by any of the majors. Second, would be, that my favorite apps weren't acquired by Salesforce.
Yes, we've done that. Especially one the slow-creep ones. Services like DataDog, Atlassian and others that let you easily just creep your costs up. But renegotiating things like DataDog also took engineering resources to cut certain things and change the way API calls were being made, etc. so it's no small feat. But it is a substantial savings (And right now that might mean another month of runway.) Most are looking very closely at churn metrics, and one tactic I would encourage, if it makes sense for you, is to ask for flexibility versus a change in terms -- for most of our applications, we know we'll still use them, but we might have headcount fluctuations. So we've had success in moving to true-up/down or flexible licensing with a renegotiation term in 12 months to give us room to flex hard in the short term, and work our way back in the long term. As always, YMMV.
WeWork isn't doing anything that most other commercial landlords aren't. If you're in a lease, you're in a lease, and they think "Well, who cares if you go under, there will be someone else who needs an office in time, so, screw off." Brutal, but I've yet to see anyone else be more compassionate (on the commercial side.) If you're out of a lease, they're letting folks go with minimal fuss, and it also depends on your overall footprint with them; if you've got multiple spaces, they're willing to be more flexible. If you're in a desk or just small space, maybe not. As always, YMMV based on your rep. Good luck.
We've been experimenting with Google Jamboard. We certainly aren't buying the hardware because it's silly expensive, but for those with an iPad, we've enabled it on our domain, and it's pretty great with Apple Pencil, and good to share with teams in a Meet chat. Works well, most folks have an iPad to use it, and gets the job done. Bonus is it can be emailed out to the team afterwards.
Administration is the absolute worst. Every panel, every screen is totally different than the last, and it's impossible to know where you "Are" in the UI.
I like that paying a bit more for ESku gives us more tools and ability when we don't have specific people in those roles yet... even replacing multiple vendors for a period of time.