I believe Haberdasher should be on anyone’s list for cocktails, ahead of Paper Plane, and it’s closer to the convention center. I could live there.
I think your “further away” list is pretty good. I would triple down on Bywater - that’s a very special place, easily the equal of places in New Orleans. PHB is a place I go to San Jose to eat at, and drink at, because the beer is super fresh and the outdoor bar in particular. Dinners are actually on the lighter side.
Re: oren’s, I wouldn’t go all that way for Oren’s, when you could go to Eureka! or Stein’s or even Tied House. I assume your assies are in computers, and Stein’s has quickly become an institution. It’s very “scene-y”. The beer list there has all the breweries you should really drink from the bay area. Cascal is a place everyone loves and I have no freaking idea why. It’s especially good for large groups on the patio. If you go to Mt View take the caltrain not the light rail — just look at the schedule, the light rail is 2x the time.
Re: Santana Row. I have a hard time eating at or recommending Amber, because the group is far-flung, and expensive, and Near just about every Amber-alog there’s a place I like better, but I don’t know about that part of SJ. Blue line is worth it, though, 100%. Love liquid bread, love Habana Cuba.
Consider: anjappar Chettinad. The yelp reviews are confused, and Assies will think they know everything about indian, but Unless they’ve actually been to south india, this place can be an eye-opener. You will get indian-style service and indian-style hassling and indian-style food. Is a ways off, though, especially depending on traffic.
Back-a-yard. This is a slightly longer hoof north from the convention center, but it’s really quite tasty.
Smoking Pig - yes yes yes. This is as close to real BBQ as they will get, although it runs a little hot and cold sometimes. Make sure they get the fatty brisket, because SP actually has it. Mmmmm. Very down-home, if they’re going to Santana Row and wotnot.
Re Burritos - Consider Angelou’s. Everyone talks about La Victoria, but the lines at Angelou’s are quite long in the evenings. They especially make a good cali burrito ( La Victoria has them too ), and you should tell them the MUST have a cali burrito ( carnitas & fries ).