Apparently Simon do play when Simon is confronted with a brother figure who she desperately, desperately wants to have in her life as a source of health and comfort.
I 100% understand this and can 100% relate. My brother I miss more than words can express, but with him and his bitch wife in my life its insane drama. Thats just my situation though, your milage may vary.
Simply, I would ask him just that "if you are flat broke, where is all of this 'spare change' coming from" as one can only have so much "spare change" and having "spare change" isnt flat broke. I may say i only have $50, or $5...but though that aint a lot, its not flat broke.
If it were me, though i quit smoking about a yr ago and went to a nicotine vaporizer, i would
never ask anyone to pay for cigs, i would go without and i would also only borrow what i had to and make a plan of paying them back likely in payments and make that plan with them and i would also spend every single waking hour looking for a job. But i also feel bad borrow anything from anyone.
Can you think of some reasonable boundries and rules? Maybe make them with your therapist, written and ask him to sign it? Explain that you need to set down boundries and rules, that not only are you not there to be used...you are a loving sister and want him in your life but you need to think of you first, physically, mentally, and financially; and make it known that you feel like you are being used and you can't allow that, but that you do want him in your life as your brother.
If you make this letter with your therapist, and also some points on how to say things, it may be received better. I did this with my therapist and my ex-roommates and i even my dad & step mom at times and it seems to be received better than what i would of said or wrote by myself.