That’s a charitable analysis I think. When developing rules people don’t think of everything. Rules around financial sustainability which don’t prevent from you generating a notional cash benefit from selling something you own to yourself don’t work. Now I agree, not Chelsea’s fault but you get into grey areas here similar to tax evasion and tax avoidance
But the issue specifically around selling something you own to yourself was investigated and approved by the PL as fair and within the rules long before Clearlake ever bought Chelsea. I wouldn’t even call the hotels thing a loophole. The PL already judged on the matter 4 years ago and decided it was OK, as long the value being claimed in the sale is fair market value.