The first step is to establish what would qualify as "turning his life around". I've chosen two requirements:
- Kevin becomes a productive member of society, loosely defined as giving more to the world than he takes to sustain himself. He can meet this just by getting a job that pays the bills.
- Kevin's life becomes fulfilling, loosely defined as a life that he could look back on in his old age and be proud of. This only applies to his life after the turnaround, as I don't think any sane person could look back at his dick chop and time spent consooming on the Tranch with pride. Achieving this is much harder, and much less likely, than requirement #1.
By far the easiest way for someone to change is for them to have a genuine desire to change, one that motivates them to do the things that are painful in the short term but lead to much better outcomes over the long term. Kevin almost certainly wants to change on some level (we've seen that in a few brief moments of honesty), but he's pushed it down and muffled it with drugs and mindless consooming to the point that expecting him to act on it is not in any way realistic.
The other way is much harder, but the only way I see meaningful change happening for Kevvie. Some powerful external events must push him out of the life he leads and into a new, better life. Kevin is and will probably remain a simple hedonist, so when these events occur he will always try to take the course of action that seems to lead to the most instant gratification for the least effort. Because of this, he will try to use any positive events on things like Transformers or amhole revisions. Negative events will have a much greater chance of forcing change on him.
First, he must be forced into a situation where getting a job is the easiest way to sustain himself. At the moment his tugboat means he doesn't need to work, so the first event would be his gravy train getting cut off. Until that happens, there's no chance that he would put effort into working. Normally I'd say that this is unlikely to happen anytime soon because he doesn't appear to be making any plans for it, but with his utter lack of concern for the future it's entirely possible that his tugboat will run out soon and he's going to ignore it until Penny starts asking about the money. Unless someone has more information about his finances, I can't tell when likely this is to happen, but I'm sure it will happen one day.
Second, he must be removed from his enablers. This could start with Penny kicking him to the curb once the money stops rolling in, or him getting left behind when the Tranch collapses. However, he will 100% run to leech off his family or anyone else willing to put up with him if given the chance. The second event would then be his removal from (or the collapse of) the Tranch without him finding a sucker to take him in. This seems reasonably likely to happen, as he's estranged from his family and most people aren't willing to house a fat man with no job and enough Transformers to fill a shipping container.
Third, he must be denied a new tugboat. At this point, Kevvie is facing homelessness if he can't scrape some money together. Living on the street would be very uncomfortable and not at all in line with his hedonistic lifestyle, so he'd be willing to go to extremes to avoid it. But before resorting to actually working, he would try to get on state or federal benefits. I don't think he has any special conditions that would make him unable to work (the amhole makes it harder but still very possible), but I believe the standards for getting on disability are pretty low so he might end up getting a new tugboat anyway. However, his unwillingness to plan ahead and the slow pace of benefits paperwork means he could end up without any money for a year+ before disability kicks in. Therefore, this is rated as likely in the short term but unlikely in the long term.
With no other options, Kevin would finally be forced into getting a real 9-5 job. His work history is nonexistent and his personality is repelling, but the tight job market works in his favor here and he could almost certainly get some kind of minimum wage retail work. Kevin would finally be a productive member of society!
The second requirement is the harder one. Kevin still has no interest in changing, so any steps towards a fulfilling life would have to be pushed on him. Here we're thrown a lifeline in the form of his weak sense of self. Kevin does not have a strongly defined personality, and will say or do whatever he thinks will get him accepted by the people around him (as long as it's not too much work). Therefore, he can be tricked into leading a fulfilling life by aping those who are genuinely striving towards one. At this point, Kevin needs positive events more than negative ones. They still can't be tangible, because any sort of money or assets would be frittered away, but he needs some good influences in his life.
Fourth is then Kevin meeting someone (probably at his new job) who's willing and able to to serve as a positive example to him. This person (or multiple people) would need to have the patience and kindness of a saint, shouldering all the burden involved in leading Kev to a better life without seeing a hint of gratitude in return. They would have to include him in all kinds of activities that meet his need for instant gratification (if it doesn't sound like fun with no work, he won't go), while at the same time showing him how you can achieve long-term fulfillment by building real relationships and helping others. This would have to start by taking Kevin out to do nerdy things together, then slowly introducing him to the idea of doing activities that involve some real creativity and effort (not that nerdy things can't, but Kevin won't put effort into nerdy hobbies without heavy encouragement). Ideally this would develop into some type of trade work, which could lead to Kevvie getting a better job, becoming someone others can enjoy working with, and maybe even participating in charity work.
He also needs to not meet any people like the old Tranch crowd until this process is mostly complete, because they'll happily lead him back into the consoomer lifestyle, and he'd easily fall back into it if he hasn't already been led to a better one. The odds of this happening are hilariously low, but if it somehow did he would be much more productive, help the people around him, and have a time in his life he could actually be proud of.
To summarize, this is what would have to happen for Kevin to lead a productive, fulfilling life:
- He loses his tugboat (likely to happen eventually)
- His enablers drop him, and he can't find new ones (also likely, shortly after #1)
- He fails to get on benefits (unlikely in the long term)
- Once he gets a job he meets a hero who shows him how to build real connections and help others, and why buying a Transformer won't make him happy (extremely unlikely)
The final odds of this happening are roughly 0%, or slightly higher if we settle for just the "productive member of society" requirement. But despite everything, I'd like to see even someone like Kevin turn his life around and I believe it's always possible for that to happen. So I'll keep hoping for the best, and in the meantime I'll keep enjoying all the lols Kevvie has to offer.