Well it's hard to gauge how he feels about all of his stuff. I'm not clear on if he is aware that much of it's likely tossed out. What's more surprising is how easily he accepted the loss of his only real lifelong human contact through barb.
Whether all of this would result in Chris starting to steal. Well it depends how much freedom a home would give him. I don't view Chris as having a mindset that's particularly conducive to stealing. Whether he would easily consider it or has some firm moral objectives against it ( which he might very well have as some of his limited moral palette).
That said if they gave him infinite freedom but never any pocket money ( and specifically prevented him from raising gibs); then yeah through desperation I could see him turning to lego theft lol
I thought he would miss his toys at first and that would be what broke him inside Jail and Prison but that simply hasn't happened, the had the shouty stompy moment in his first court session about wanting his stuff before he felt safe (parroting words an phrases he's picked up from the trans groups) but that was mostly because he just bought it so he hadn't had a chance for the novelty to wear off and end up as part of the horde.
His emotional salve is getting a new toy, rember Barb bribed him into talking by buying him toys if he could pronounce the name if he did anything positive he got a reward, or if his sulks had too much of a impact on her she gave him a toy - it's not really the toy that he hankers after (although that is part of it) it's the endorphin rush of getting a new thing.
It's almost a kin to the guy who's always been just above the poverty line not because he's got a shit job but because he's terrible with money and trying to keep up with the Joneses suddenly winning the lottery who then goes on a massive spending spree for a few years on luxury items like cars, watches, wine, women an song only to end right back where he started a year or so later with nothing to show for it - it's not the money that's a problem it's the addiction to getting new stuff so it's always the newest and best.
Chris has a big sense of self entitlement, if he's denied something long enough that he feels he's deserving of or entitled to like the Art award in school, toy's, games etc he has no problem taking from others like when he stole from barb and bob in the past, taking out lines of credit with no intention of paying it back, and the odd occasion he's tried to steal so far, hell he's tried to con people into sex in the past like when he pretened to be liquid to Kacey, or when he tried to guilt a hooker into fucking him (pre Mia Ham). He thinks his needs over ride anyone else's wants, needs and rights because
he deserves it - if you limit his legal access to things he wants by restricting his access to money (much like bob did when he first stole from them) he will find a way of justifying himself stealing and act on it especially if he's not had a fix in a while.
Barb's life more or less culminated and ended in a series of rapes and her retarded rapist son is the only thing anyone will remember about her.
She lived a sad sorry existence mostly of her own making, no friends, no family, no social life, nothing youd just have if you where a OK person let alone a "Good" person. I think that's going to be the saddest part of her life when the scales of Karmic existence are judged in the afterlife there is nobody who isn't legally or morally obligated to get involved with her of their own volition.
She didn't deserve to be raped nobody does, but Chris was a problem of her own making to a very large extent she never tried to get him to do things that would be benifical solely to him she had to benefit in some way as well - there is a call I can't recall the name of now where she chastised Chris for not doing anything around the house and she had to do everything and she wanted him to start pulling his weight, from the outside that was perfectly normal and acceptable but this is when the house was in full on horder mode so she wasn't doing anything but sitting down, watching TV and reading etc and at the time she was far more active and functional than she is now.
She never encouraged him to behave or at least moderate his odd behaviour outside the home because as long as she wasn't effected it wasn't her problem if anything she was glad he was out and doing his weird shit away from her because she didn't even have to pretend to care about his well being.
Chris was never going to be normal this was clear from a young age but he was allowed to get as bad as he has because she was mostly disinterested in him developing and viewed him as a helper monkey at best and a embarrassing burden to her at worst. Bob wasn't much better but he atleast tried in his own misguided way to get Chris to at least try but even he gave up and with someone like Chris it's a whole family effort to get them to have a glimmer of normality.
Chris hasn't been funny in years he's been that really bad car crash you can't quite take your eyes off no matter how many pretzel shaped people you see tangled in the wreckage you just need to see how it ends and it ended with a bigger mess than anybody ever thought could or would happen.