I think the problem for Randy is that he only wants to fight in big fights that would bring huge crowds. This means either title fights against Lesnar at HW or dropping down to challenge Machida at LHW or fights like a catchweight fight with Anderson Silva or a big name like Tito Ortiz. Problem is he isn't a top contender to get those fights anymore and UFC would have to leapfrog the top contenders to give him these fights. Then in the end he really can't beat these guys at this point in his career. I understand him not wanting to retire or be relagated to a journeyman or gatekeeper status, but truthfully, that's where he needs to be right now. I won't take anything away from him though, he always comes ready to fight and it's hard to count him out.
You're right. Randy is the Bruno Sammartino of MMA. I don't expect to see him win in a fight, although if he winds up fighting all six, he might pull one or two out. What I expect to see is him playing the part of the old lion--defending his legacy with dignity and courage. UFC's media machine got Chuck a lot of attention but, regardless of his losses, I just don't think that he had the charisma to hold the spotlight. Lesnar and Tito (if he returns for any length of time) are heels and can only take the promotion so far. Randy--or at least the media version of Randy--brings gravity to the sport. Every penny that Zuffa pays him will make money for them.