Let's make some fairly likely assumptions:
-Barb dies in a way that is obvious that she is dead.
--Chris isn't to blame or culpable for her death.
--Barb dies slowly enough that she can make last requests, etc.
The obvious person to turn to is Rocky Shoemaker. Rocky will definitely ensure there is a funeral service, although Barb probably left no real funds for her own funeral. It's actually not impossible that Barb dies with no way to pay for her own departure, and so a Funeral Barge accompanies the Tugboat as you and I pay for Barb's final rest.
Barb's funeral is a very sad event. The Hollywood answer--that Barb's family, her former lovers and various old workmates of hers appear in a gathering that gives Chris some contacts and a way to make a future--isn't going to happen. It's actually fairly possible that the Troll delegation is the largest and most meaningful at the funeral; alternatively, if the CWCki decides not to do anything here, it might be a terribly empty scene of saying goodbye to his mother.
Losing a parent is rough.
Losing your own acquaintance in life is extreme.
No one should be betting on Chris getting through this easily. If there were no other factors, this would be at least as difficult as losing Bob. But Chris' life is more fundamentally disrupted than just the death of Bob Chandler.
The next question is money. 14 Branchland is owned by Barb; the mortgage needs to be paid, but the equity in the house may be Barb's most expensive obligation. Chris could wind up homeless if the house is seized. When Barb Dies, all of the games that Barb played to keep ahead of an ocean of red ink die with her, and Chris' possessions might be very limited. He has Son-Chu; He has a Tugboat, he doesn't necessarily have much of what he had even after the fire.
The Mortgage company isn't likely to evict Chris immediately and he'll need to make a decision of where to go or what to do. This is the first question that is likely to make a massive shift in Christory. Where does he go? Urban life might suit Chris for its general ease in getting food, fun, and social services, but the rent is likely higher. Rural life would give Chris the isolation he seems to enjoy but would definitely shrink his Moobs as he's forced to travel further.
Even CWC is going to be forced into social interaction. It's NOT POSSIBLE that he's going to be utterly isolated. With no Barb, his desire to avoid confrontation is all that stands between him and disaster. If he tries Legal Saga III, he's staying behind bars no matter how badly he confuses the situation with rapists in dark alleyways. I can't rule out that Chris is more likely to go Blue Arms Stupid over the dumbest ideas and get into trouble.
What Chris isn't likely to find, and this is the hard reality, is anyone to accept him or support him. He reaps what he sows but the harvest is a very bitter one. He will remain single; he will eventually alienate the LGBT community that has forgiven his animosity. In the long run, I think it's around a 3-4 year cycle before Chris commits another Felony. Chris repeatedly commits crimes, and on the whole, he's been lucky. We should not forget that:
1) Chris flouts bans. This is Trespassing, and Chris has probably committed this a dozen times.
2) Chris generally commits multiple criminal acts before he gets busted. 10/28/11 follows a similar incident in June 2010 that played out in nearly the same way. Blue Arms Banditry followed a criminal nuisance campaign that involved glitter bombing SEGA and hiding Sonic Boom merchandise. Chris' treatment of women may well qualify as harassment--unwanted touching or otherwise making them feel uncomfortable.
3. Chris is, in spite of all his stupidity, still believes he's godbear's gift to the world. He doesn't even need to be self-consistent or coherent, but he's always right and eventually this will lead to problems.
4. Chris is profoundly lazy. He will not improve himself unless there's something obviously in it for himself--and what happens in this regard when he learns there's no China in Tomgirlworld?
I think Chris eventually makes mainstream news for a particularly stupid act. It may be a Darwin Award, it may be the Felony that gets him 5+ Years, but he's not going to live a normal existence.