I have worked hard and lived a frugal lifestyle my entire life. . .and been fortunate to do a number of things right and not too many things wrong. My family lives far away and they have no idea of my net worth. They may have some inkling because I have taken some awesome trips, but I have never shared any numbers. No one has asked for money, but I have been generous mainly for graduations, weddings, showers.
In my travels, I have made it a habit to leave money on a daily basis for housekeeping at hotels. I figure those extra dollars will make an impact in the workers lives. When I frequent restaurants and have excellent service, I bump up the tip to 30%. I do this in my hometown especially when I visit family run restaurants. I know a gentleman who drives a taxi and can reserve a date and time with him a week ahead of time. I tip him well. These are small amounts for me, but can impact low wage earners.
As far as gift giving to others, I like to receive some acknowledgement or thanks for the gift. I was an educator and frequently gift books and supplies to individual teachers. One sent photos of the students with their books, another had the children hand write thank you notes, and others send an email note. If I do not receive any acknowledgement, I move on and find a new recipient.
I put a great deal of thought into how to structure my will since I am single. None of my relatives are in dire need of funds. I do have one brother and SIL who Tend to be a bit greedy and jealous at times even though they retired at 50 and have a great life. I feel no obligation to leave them or my other relatives any money. If there is anything left after I die, it will go to a foundation to be distributed to teachers for classroom projects and some will go to scholarships for students in my home county. Making those decisions took a great deal of thought and time.
I have enjoyed this thread and learning how others have handled this situation.