These sayings arent universally applicable but people tend to apply them as such. Heres my take.
Afaik Stay humble stack sats is simply meant not to boast about your stack. Just stack, its no one's business but your own. Humble isn't always meek. Humble can be quietly strong. I define humble here as not to boast and to do things in a principled way without seeking fame or attention.
Have fun staying poor - its simple. You can lead a horse to water but you cant make them drink. Have fun staying thirsty.
You can be humble and help friends and family find bitcoin. If they don't get it, sorry hfsp I guess. It is humble strength to help someone in need without seeking return, but also to be able to eventually step away and allow that person to ultimately help themselves (or not as the case may be.)