Downside: Not to be all man about it, but sometimes it's nice to be first.
Ok. That's funny (!)
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I will try to keep a lid on my own fire. Money is always a hot issue, whether you've got it or not. I was raised spendy, but I was also raised not to be greedy. I've had to work on not getting on people's nerves with a reluctance to accept when they suggest buying something for me. Reject the gift, reject person - or so life has implied it to me.
Anyways, continuing on about being raised spendy... This has been what my life's experience has suggested:
There IS a point of diminishing returns. A threshold above which a dollar's increase in price brings less and less in terms of value to hang your hat on. The threshold, however, is not universal for all items. Different things have different thresholds. $1000 of food is not the same as $1000 in rent. $1000 dollars put towards food could last you several months. A $1000 put towards rent - I'm not sure you can even get into a place with only $1000, considering you need to put down deposits etc.
So I would fly to another city for a meal prepared under the auspices of one specific chef in this world, but I will not spend more than $30 bucks on a suitcase ever again. Suitcases used weekly will need replacing at the same rate, whether $30 or $300. And, frankly, when the monkey back in baggage handling is done jumping on it, you will feel less distraught over the loss of the $30 one. No beauty has been destroyed.
But you know, go to Vegas and have this one meal - and honey, you're done. Life is complete ;>