The primary obstacle in his plan... is that it does not take into account that the core business is failing. It requires selling off at least $1.5B of "encumbered" real-estate to pay creditors; commencing 1st with secured creditors. It mentions paying ESL last; but in so many ways he has already looked after ESL first by paying off his shorter dated bonds in recent PAST asset sales. (And ... non secured creditors would still be behind ESL for any payments. Some are asked to forgo future interest payments ; accept worthless PIK; or simply convert to equity. Non secured creditors are asked to take a bloodbath.).
Did I mention these are "encumbered" assets?
It is a long term plan; supposedly so a fair value can be wrung out of real estate sales. He ACTUALLY states a minimal value is assured; but that's simply totally untrue. I presume the stated value of assets are based on ESL's OWN APPRAISAL!
Let's assume in the 1st quarter $500 million of "encumbered" real estate is sold. There will be a hefty cost to un-encumber the properties... but let's ignore that. The intent of the plan is to pay back creditors with the $500 million from the sale. BUT with a quarterly loss of over $500 million there is nothing to give to creditors. He can pay creditors; or he can [have already used the funds to] pay wages and the utility companies that keep the lights on. He can't do both; and paying creditors with the funds is game over because the electric company won't keep the lights on and workers do not work for free.
It is a 3 year plan; but if he cannot pay any creditors after the 1st quarter.. he cannot even get into the end of the 1st year in his plan.
So.. even though his plan clearly defines paying creditors over time by sales of SHLD's final holdings... it simply is not possible from a failing business holding dilapidated; encumbered; properties.
*A good analysis of Eddie's restructuring plan, made by @VmNYA2G-yxu *