I don't think that we will ever know for sure what Eddie Lampert's original intentions were. I suspect it was along the lines of attempting to do something that few had done before & come out successful. It probably became more difficult than he had anticipated.
Those pesky Sears stores with all those loyal associates became a stumbling block. Why didn't they just leave? He would have. Additionally the public sentiment of growing up with and feeling a fondness for Sears limited him PR-wise from shutting the whole thing down, selling off the venerable brands, and just using the real estate all at once.
Finally the combination of older/immigrant Sears shoppers not buying over the internet and having a poor functioning website kept the business from becoming asset light at the pace he planned.
Transformations are tough when you talk out of both sides of your mouth. You aren't truthful with your stores or corporate office that you're shutting down and you're lying to your investors a la Berkowitz's that it's all about real estate value.
The interesting things to me is: Only one man is behind all this yet many SHC workers and supposed investment savvy types like Berkowitz wanted to believe the scenario that best suited them for so long that this mess is where we are in 2018.
Posted by @RD7cXcx-2tat, really well laid out.