To a large extent, I think Ralph has been his own worst enemy, and I think it has less to do with finances as it does his ability to get along with highly motivated, succcessful and aggressive football people.
Looking back at the Bills' history, Ralph has had problems with Lou Saban (twice), Chuck Knox, Bill Polian, John Butler....most of the people that have been successful for the Bills have left over disputes with Ralph (or so it seems from my recollection of the events leading to their dismissal or quitting). Ralph has made some horrible decisions (appointing Harvey Johnson interim coach TWICE, hiring Brandon to be GM, Stew Barber to be GM, etc). Ralph also has had some bad luck in hiring guys that on paper looked to be pretty smart hires (John Rauch, Donohoe, even Gregg Williams). Whether he is too meddlesome, or reluctant to hand over authority to the professionals he hired, Ralph seems to have caused more problems via his management style than via his wallet.
That being said, he HAS kept the team here for 50 years and he HAS hit the jackpot with hires that others ridiculed - Levy, Nix, Chan (ok, maybe its too early to say he hit the jackpot on the latter two!).
I'm just glad all of my professional decisions and financial actions aren't out there for everyone to see and criticize
Whether Ralph has a succession plan in place or not will have little to no bearing on my enjoyment of this coming season. I am glad he felt compelled to spend a bunch of money on solid acquisitions that should really help this team succeed this year.