[MichaelMcG]

Good points, I basically use the same strategy with a few exceptions:

Re: #2 I don't like to focus on conversations related to occupation, I've found people start to open up much more if you focus on who they are/what they actually enjoy doing outside of work, since most people don't like to be defined by their occupation. The random outlier being they work full-time on something they are really passionate/care about, but that is fairly easy to figure out if they mention it as how they spend their free time, or in rare cases they mention it due to the position being (in their eyes) a status symbol e.g. my college friends on Wall Street in IB/PE.

Re: House/car values, I've found people get real weird discussing values and it's sort of 50/50 on commiserating with you/being annoyed about high living costs. Some people love humble-bragging that they can afford to live in/own property in a location 2x * U.S. Avg CoL, others get annoyed you are apparently bragging about your affordable location. One of those things you'd have to play close to the chest. I think it all comes down to if they mention hating the high CoL where they are and their desire to move.