@riss, Here are my thoughts on what you said before, I have a bit more time to write now as I am done with my meeting. I'm 28, so not too much older than you, but probably a significantly different perspective on things. It might sound cool to drop $5.5k on a Brioni suit at Wilkes, and it could feel nice to be catered to for a couple hours, but once you get home, you have more or less the same thing that you could have by paying $1500 on ebay or at Filene's. I have paid cash for expensive items in the past, but it doesn't feel "good" for me to do so, even if I can afford it, I feel like I am somewhat ripped off, regardless. This happens whether the object is expensive or not, it's probably a personality trait. I have a fairly loosely budgeted amount of money set aside for traveling, clothes, vacations etc, and would like to get the most out of it by getting the best value for my money. I have a habit of spending a large amount of money at restaurants and hotels, which you can't get substantial discounts on for the most part, and would like to maximize my ability to do so. The majority of my income goes back into the real estate market as I prefer to spend money to make more
I don't think I would change my lifestyle too much if I had 10 or 100 times as much money as I currently have. I would likely still work, as I enjoy building (and sometimes selling) companies. I may travel a bit more than I currently do (although I am away almost every weekend) and go a bit farther afield for a longer period of time, but not too much else would likely change.