These are all great questions. However, it is important to understand why you're asking some of these questions. For example:
- Runway left and when was the last raise: are important because you'd like to know when the company will run out of cash, but more importantly perhaps is to understand whether there's a dilution hit on the horizon so you can negotiate accordingly.
- Equity and the vesting schedule details..: if a startup company doesn't answer or provide you these details when you ask, then you might want to reconsider joining them. Getting 10K or 20K options might seem like a lot, but without knowing how many shares are authorized and issued you don't know how much equity you're really getting.
Most early-stage startup employees should price the equity grant at $0. If everything works out great, it'll be a lot of money you can't do anything with about 5 years from now and often only turn into actual cash a decade or more out. In the meantime, your personal finances has to work based on the cash salary you receive, without any raises (because "raises" for a start-up are achieved through equity grants becoming more valuable).
Yes, the grant has a positive expected value. This value is too uncertain and too illiquid to significantly affect your planning, which ought to care a lot more about what the maximin strategy suggests for your course of action.
- Runway left and when was the last raise: are important because you'd like to know when the company will run out of cash, but more importantly perhaps is to understand whether there's a dilution hit on the horizon so you can negotiate accordingly.
- Equity and the vesting schedule details..: if a startup company doesn't answer or provide you these details when you ask, then you might want to reconsider joining them. Getting 10K or 20K options might seem like a lot, but without knowing how many shares are authorized and issued you don't know how much equity you're really getting.