After about a decade at Sears, from being in the trenches at the store to meeting with VPs, I think I have a pretty good idea of Sears and its downfalls.
First and foremost Eddie cannot lose, short of going to jail. He has money and control, and will always stack the deck in his favor. Trying to keep Sears as a retailer isn't going to happen, and not for the reasons you would think. To revitalize Sears you would have to take risks, investing in stores and infrastructure, Eddie won't do this. Sears is worth more failing as long as it fails slowly.
Think of Sears as a ship loaded with cargo, (inventory, brands and property) if you know repairs to your ship would cost more than buying a brand new ship, the smart thing to do is buy a new ship and move all your cargo over... but that takes time, but is lower risk than anything else.
Inventory: Sears has been cutting back on inventory as well as purchasing "off price" merchandise to resell. Additionally they have been moving back to owned DC vs outsourcing DCs to give themselves more control over the inventory without outside eyes.
Brands: Sears no longer owns its iconic brands, Kenmore, Diehard and Craftsman were sold to another corporation that Eddie owns called KCD, they then required Sears to pay a royalty to use the brands (from my understanding this royalty was actually higher than outside brands like disney and such) additionally I believe they have outright sold the rights to at least Craftsman and DieHard to other companies.
Property: Sears sold multiple locations (or have property backed loans) to a REIT company called Seritage (want to guess who owns that one? If you guessed Eddie... ding ding ding) Sears then leases them back, to keep the store afloat to keep the value of the property up until someone wants to buy the location, then the store gets closed for "performance" reasons
Eddie keeps playing both sides of the deals, funneling money out of Sears and into his other investments. I have even heard this about IT as well... as he has part ownership in the Offshore IT service, so he can layoff more people and funnel the money and work to India.
Eddie is going to keep this ship afloat until he can s--- all the value out of it, then let the husk crash where it may.
There are only 2 ways for this plan to fail, everyone quits before he can sell everything, or he gets found doing something illegal. That said, I think he is greasy enough and smart enough to stay just on this side of legal, while straying far past the line of morals. My prediction is that after this all goes down, new laws will be created from allowing something like this from ever happening again.