You have mentioned some of the things you feel you are lucky to afford, like multiple homes and trips. But what do you LIKE about your expenditures, other than being able to afford them? Does one or more of your homes have a terrific swimming pool, surfside view, easy access to the many shops and restaurants of a major city, ballroom for inviting hundreds of friends to a dance with live music, or what? Did you especially enjoy seeing the Parthenon or the Mexican pyramids or the black sand beaches of the Big Island? I get the sense that you just like *having* money but that really you aren't finding much satisfaction in spending it. I hope that is not the case.
Thanks for your concern. I think you might be mistaking a tendency on my part to describe our lifestyle in somewhat antiseptic of impersonal terms with my desire not be seen to be bragging or being smug. I assure you I enjoy our lifestyle very much. I hope no one takes this post as bragging, certainly not my intention, but I felt I should respond to your post.
Never been to any of the places you mentioned but have been to lots of others. Our trips since retirement have generally been of the active type. Just got back from an excellent biking trip to Umbria, Italy. Great biking, great food and wine, great friends. Other trips have included friends and family on cruises, Europe, Turkey, Southeast Asia, etc. I really enjoy our travels and they tend to be expensive. Have another biking trip to Bavaria and Austria planned for September with a group of friends we met in Arizona.
Our homes are indeed enjoyable. The Arizona house has a very nice pool and gardens. This place is our winter respite from the harsh Canadian winters. Have met new friends and enjoy the excellent restaurants. Our house near Banff offers world class scenery, biking (both types), hiking, skiing ( also both types). I sit on a not for profit board there and have met some wonderful people. Our Lakehouse is our place to get some quiet solitude in a natural setting. Great boating, water sports, fires in the big stone fireplace in winter. We use this a lot for entertaining our family who are still mostly based in Ontario. Lots of fun there. Finally, our Toronto condo is right downtown and walking distance to both major sporting venues, opera house, live theatres, and at least 100 restaurants. Don't spend too much time there. Mostly when we visit our parents who live in Toronto, but when we are there it has an eclectic urban vibe which we enjoy. It also serves as a staging point for visits to the Lakehouse. We often loan our places to friends and family. None of our places would accommodate 100's of guests as you suggest. Wouldn't be our style anyway.
As I said, I am really enjoying our retirement lifestyle. Not suggesting for a moment, that others would or should. We have built this lifestyle over several years since retiring, and although we currently are having a ton of fun, I can certainly see how we will need to simplify at some point. Hopefully we will still be having a lot of fun whatever we do.
I can also see that retirees can have just as much fun for a lot less money. After all fun and happiness are very personal things. But I reject the idea that having more money somehow makes it less likely you will be happy. Certainly money that has come from a lifetime of working when used to generously fund a retirement can help make someone happy and secure. I also reject the idea, sometimes discussed here,that there is a universal "sweet spot" of wealth. Each person decides on their own "sweet spot" which can be quite different from others. Not surprisingly these so called "sweet spots" tend to be around that person's actual wealth.
Again, I apologize if this post seems smug or bragging. I also hope it doesn't sound defensive.