I would suggest #1 is not Something DL should be faulted for. At that point you were a standby passenger, not a confirmed one, no way should they pay for two VDBs so one standby passenger could get on the plane. Actually, I'm not sure why they would even VDB one for a standby to get on, as standby is just that.

#2 and #3 might be worth an email. I would not expect DL to pay for expenses, it is rare that you even got a hotel voucher for weather related mishaps. I would expect miles or a tcv, but no out of pocket reimbursement.

I would seek a refund through whoever you booked the hotel with. And yes, it gets much harder to book rooms for that night once the clock rolls past midnight. Even if you find availability through a third party site, I would always call the chain if not the exact hotel just to make sure nothing gets screwed up.