There is already a certification process for helicopters and autogyros, so VTOL capability alone is no reason for a different certification process. Helicopters require a 20 minute fuel reserve in VFR conditions and 30 minutes in IFR conditions.
Yes but these are automated, so they could be programmed to stay within X minutes of backup landing sites at all times, and altitudes to reach them easily.
No there will be a human pilot in control. It's going to be many years before fully automated aircraft are allowed to carry human civilian passengers through regular airspace.
https://www.law.cornell.edu/cfr/text/14/91.151