I don't get this either.
I don't think Gilbert is taking some low level assets and/or draft picks that are long shots to be really valuable to take on dead money when his team is already in the repeater penalty on the luxury tax.
What you are saying and what I am saying aren't in conflict. I think the actual value of facilitating a Lebron sign and trade is somewhere in the range of a couple late first round picks. That's what Cleveland got last time. That's essentially what the Clippers got for Chris Paul just in terms of present players rather than future assets. (Lou Williams and Patrick Beverly are probably of roughly equivalent value to a late first each and the rest of that deal was mainly filler.)
That said, that has to be the net value of the package. If Houston is taking back dead money, they have to be compensated for that too. Thus, the Houston conversation has a pretty steep draft pick price tag because they aren't just trading for Lebron, they are trading to get out from under the Anderson contract. Anderson's negative value is probably in the ballpark of a couple late firsts. Cleveland can probably bargain for Houston to do what the Nets did and not protect the picks, which may pay dividends on the back end.
With Philly, they don't need much help, so the return would be a lot lower. Bayless is a bad but expiring deal and doesn't make that much anyway and is really all they need to unload.
For Boston, any of Irving, Hayward, or Horford have more than enough positive value as assets to exceed the return expectations for this sort of deal. Whether Cleveland would ultimately spin them off for future talent or try to keep their roster together and reload is anyone's guess, but in either pathway, the Boston centerpiece delivers more value than what they are likely to get from anyone else and more value than the standard market return for this sort of deal.
To sum this up, my posting has been pushing back against the idea that Cleveland will be able to play teams against each other or get something like the #10 pick from Philly or the Kings or Memphis pick from Boston. I think all of those assets are too valuable for the context of a sign and trade deal.
Also, to those who will point to Gilbert, I suspect the Decision left him feeling a lot more vindictive than Lebron leaving this time will. And, even then, he ultimately agreed to a sign and trade, at the value of a few late firsts, and in a world where late firsts were viewed as significantly less valuable assets than they now are.