Sociopath Community

What if someone was aware of others struggles and still chose to steal selfishly for fun, or the fact that others struggle bring him fun, or maybe even the fact that other people get wind up over it bring him fun?

because it certainly sounds fun atm

"What if someone was aware of others struggles and still chose to steal selfishly for fun?"

I would hope that individual would look for more productive ways to enjoy themselves. The only way I see stealing as a viable option is under one of these three conditions. 

1. Person is poor, needs the items that by any other means besides stealing are unobtainable. 
2. Person is stealing large amounts of money(bank heist, Nigerian Prince scheme, etc.)
3. Person is a diagnosed kleptomaniac. 

What if what they stole was insured by the store? An arguably negligible loss they won't even miss?

It's still a heavily, self destructive behavior. 

I can't see a immediate, temporary gain over the likely, possible repercussions. 

So you're judging others for their recklessness then? Is ignorance even a factor here?

I works both ways and I discriminate against both parties equally. 

Recklessness because the person isn't mature or responsible enough to control their own impulses and emotions even when threatened with steep repercussions. 

Ignornace simply because they assume what they can't conceive. 

EDIT: Usually the two work hand and hand, encouraging eachother. 

So thievery to you shows a lack of self-control when faced with risk? Interesting.

What about con-artist thief types, people who can talk others out of their possessions, or are masters of subtle sleight of hand? When they have made stealing into not just something to do, but a talent of theirs? Those who may very well recognize the risks, using them to push themselves to become better thieves?

If you can remove the consequences then I see no problem. 

However, I don't think people who've reached this point do it for a thrill, more so for a ego boost. 

The consequences would still be there, but the consequences themselves would be their motivation to become a better thief, not drop the activity altogether (similar to something like skydiving or bungee jumping). If they became infamous for it, the risks would arguably become even higher.

Is the ego boost itself... not a thrill? It has to be causing some sort of adrenal response, even if practice has reduced it's displays.

If the person has perfected their craft enough, then petty thievery probably won't give them much of a rush. They would continue to challenging themselves,  escalating the stakes until they were stealing a considerable amount of money. This would fit my criteria.