On H1B visa. New to US. I need some information on what other H1Bs are doing related to finances, buying a house, green card etc. Unfortunately, only people I know are the ones from my office. I have tried meetup apps and still have not gotten anyone with experience in the topics that I have mentioned. I have some senior collegues who are/were on H1B. Is it okay to ask these personal questions? All we have are office team lunches. When to bring up these questions? How to keep in touch with them even after we leave the team/company?
I'd start with what commonality this group has, which is easy in your case -- other H1B visa holders. (If there's nothing in common, it's much harder to strike up casual conversation and friendship.)
Is there a social channel or group within the company? It sounds like the types of questions you want to ask are less about getting a concrete answer and more about getting multiple samples, and potentially just creating a friendship.
So I'd phrase your question as, "Here's the type of person I'd love to learn from. I've tried X and Y but they were insufficient for these reasons. Anyone up for a chat?"
I definitely wouldn't put your personal questions in the post, but you want to portray that you've done the legwork and would like to have some discussion (as opposed to people pointing you to documentation).