The Fall of Del Rio

I'm still a huge fan of Del Rio's in-ring work and ring psychology but it appears that the crowd couldn't care two cents about him if his life depended on it and I was wondering where did it go wrong? He was progressing nicely after his debut and I didn't mind him winning the Rumble. After he lost at Wrestlemania, he seemed to be in a funk until winning MITB. And we all know what happened once he cashed it in. Do you think things would have been better for him if he had won the title at Wrestlemania or that he waited to cash in the briefcase? Also, why don't they do more with his character when the opportunity is right there in front of our faces? He's rich. Use it more to his advantage by paying off guys to do his dirty work or bribing referees or something. 

I feel like we've discussed this one a few times already, but yeah, I think he would have been 100x better off beating Edge at Wrestlemania to win the title instead of losing there and then losing to Christian and then losing to Cena and then losing to Punk.  The original plan had been Del Rio winning the belt and then dropping it to Orton right away, however, so either way he was kind of boned.  
And just ONCE I'd like to see him buy a better spot in the Royal Rumble ala Ted Dibiase.