It sounds like boss is trying to set you up for success by including you in an important conversation, maybe wasn’t expecting it to be a big deal to you, wasn’t

It sounds like boss is trying to set you up for success by including you in an important conversation, maybe wasn’t expecting it to be a big deal to you, wasn’t expecting you to push to accelerate your start or to get an invoice for time (both of which will cause them effort outside the normal onboarding flow, and invoicing particularly will probably be “weird” procedurally). They didn’t give you particularly polished answers but I wouldn’t infer from that they’re an unprofessional manager — likely the first time they’re encountering this in their career? FWIW: I’ve led organizations of 250+ people for years and can’t remember running into something like your situation in that set of experiences. If we had, then we’d likely have just delayed the vendor calls until you were on board, however, <500 companies often have ‘task urgency’ where >25k companies just say “Another 3 weeks won’t hurt much”. Subject matter expertise is always nice to have in leadership for sure but isn’t guaranteed. I’ve no idea your skill set or that of your new manager but particularly with larger teams you’ll invariably have multiple disciplines, of which they’ll be more comfortable with some and less with others. I think you’re reading too much into IT mailing your productivity equipment - all the usual suspects like FedEx and UPS support “Vacation Holds” as well, so you could likely have taken off and everything would have just been there when you returned. “Unlimited Vacation” at most companies is a bit of a trap. Primarily, in my experience at least, it exists to avoid both process overhead (tracking time) and financial liability (since accrued vacation counts as such). Many US companies still train their managers to expect the amount of time someone takes off to be roughly equivalent to what they had in vacation days before the switch to “unlimited” occurred, so 10-15 days PTO, and 7-10 observed holidays. Maybe a handful of sick or personal days.