I'm currently on disability, but last year I was in the Army. I didn't have to worry about being passed over for promotions and such because of my REI and the perception that I didn't need the money.
It usually didn't come up because I don't manage my own stuff and was never even in the same state with it, so unless I was looking for property or something, it just never found it's way to conversation.
When looking for property, I tend not to tell people who are bad with money. Obviously, if I can afford to buy a house, I can afford to lend them $200 til payday, so I should lend it to them. Things get sticky if they perceive that I'm rich. But for those better off than me, it wasn't something I kept as a secret if it came up in conversation.
Now that I'm on VA disability, people think I'm scamming the system if I have real estate and get a disability check. But they are completely separate things. I can work full-time and still have a VA disability check. It pays for damage from the Army, not because I'm not capable of working. But because I'm currently actually not capable of working, people see me as one of those people who lives off a government check and is investing in real estate at the expense of their taxes. When I'm back to a full-time job again, I'll probably go back to my former way of handling it...even though I'll still be getting my disability check. Like I said, for VA disability, it's not related to my ability to work, only damage done by the military service.