Very few of his business endeavors actually make any money. Chris is not bright. He does not consider losses or gains. He lives in the now. He gave away hundreds of dollars worth of crap for his eBay contest scheme, but the actual sales that mattered were meager. He made his money on the shirt or some other piece of garbage.
No, this is incorrect. Almost all of Chris' business endeavors make profit. There are exceptions, and they're prominent and hilarious, but they are not the majority.
When Chris begins a business venture, he does the simple arithmetic where he calculates how much it will cost, how much he has to list it to to make money, and he goes and does it. Most of the time, he makes a small profit.
Chris can pay bills if he gets them, but only if there is money. He does not understand money enough to manage it.
This isn't true. At the beginning of the month, Chris receives his tugboat. He knows he has to pay certain bills every month, like internet, phone and insurance. It's not just a matter of a chance occurence that the money is in his account when the bill arrives. Chris actively plans for the end of the month, in the beginning of the month.
So if he's got a reoccurring bill for $X that comes on the 25th, Chris has that bill in mind when the tugboat arrives on the 3rd. Every month, Chris remembers that he needs to have a balance of at least $X by the 25th.
Chris has been doing this since Bob died.
Chris keeps garbage that is worth nothing to him. The reason that some stalker found all the old crap they threw out after the house burned down is because the Chandlers all thought holding on to worthless crap was important.
It's fairly normal to save things like school papers and report cards from childhood.
Since it barely takes up more than a box or two, people's parents will stick them (along with yearbooks and similar trinkets) in the basement and forget about it. It's not unusual.
Chris is loath to get rid of anything that he likes. When he sells something, it is something that is not his or that does not mean anything to him.
No one likes to get rid of things they like. Chris' standards for what he likes are like a spoiled child who has never had to get rid of anything.
Furthermore, in response to greater financial pressure, Chris is willing to get rid of more and more things. Nothing is particularly exceptional about Chris' attitude towards his possessions.