You will need to fit into one of those positions (if it makes you happy) or leave. You have a valuable set of skills and it's a great time to work on your own ideas.
>> i.e. how stressful is too stressful, until multiple outside people and coaches I was working with remarked to me that I looked incredibly worn down for months on end and it wasn't supposed to be this hard.
@sama did just tweet about saying you look tired[1].
just imagine what all those ISPs and hosts who are not on the private list but who use Xen are thinking. They must be crapping themselves, hitting F5 on the announcements page, ready to pounce and fix.
don't forget to add costs for getting TO the airport. BART costs ~$15 (for either Oakland or SFO), by cab (Uber) ~$50. So while $250 might be on the upper side of things, I think $150 isn't exactly right either. so the low $200 range.
I am currently in a similar boat as you.