NorthOntKid,
Good questions,
We must not forget that KRY is the only judgement creditor not subject to the OFAC sanctions. This is the case because KRY obtained the collection judgement lien on Aug. 24, 2018, and the sanctions on PDVSA were issued in Jan. 2019. In addition, KRY's judgement went all the way to the SCOTUS and, according to Judge Stark and the Third Circuit, "every day that goes by without KRY being paid is an affront to the Judiciary".
Also, as we have learned over the last few years, anything can happen in this case. It cannot be ruled out that the U.S. government will not want to allow Venezuela to lose CITGO until the political standoff down there is resolved. Why? Because there is a power / leadership void in Maduro's banana republic where no one is actually in a position to deal with this issue and assume the responsibility for the great harm to the Venezuelan economy and people that represents Venezuela losing CITGO.
Thus, it is possible that the U.S. Treasury / Executive could decide they cannot allow the transfer of CITGO's ownership without causing great harm to its foreign relations policies. In this case, the judgement creditors subject to the OFAC license requirement to allow CITGO's ownership transfer will see their collection efforts delayed until the U.S. Government is ready to transfer the responsibility for Venezuela losing CITGO to whoever is determined to be the legitimate president of the country.
The foregoing begs a question: how can KRY collect its judgement without the auction taking place? The DE District Court has the inherent power to order the allocation and issuance of CITGO shares based on the best bid received. Each judgement creditor can then deal with their shares in a manner and time that best suit their interests. The question then is if the winning bidder is willing to buy the shares and wait until the OFAC License can issue.