CW: You may be overlooking something here, and that is the fact that all the acts of God/Jesus, besides taking place in our historical time, are also outside of time, as God is outside of time. In the same way that the sacrifice of Calvary, the act of our redemption, is made present at each Mass and not ‘repeated’ over and over again (because this sacrifice is always present to God in the “eternal now”), and in the same way that the Immaculate Conception of the Mother of God was due to the merits of Jesus’ death and resurrection and was her redemption (same as it was our redemption) was accomplished by God by applying those merits “in advance” of the historical act. Because God is not bound by time and because the merits of His acts can be applied - by Him - backward, forward or in the present - by His decision and power, it is possible that the good thief was, indeed, welcomed into heaven, as Jesus promised him, prior to the actual resurrection ‘in time’. I don’t believe that parsing the words ‘heaven’ and ‘paradise’ proves anything or is even necessary, because there is no conflict in Jesus’ statement even if He DID mean heaven or ‘seeing the Father’…
Most take Jesus’ use of ‘paradise’ to mean ‘heaven’ and there is no conflict when we understand that God is not bound by time and that God could, if He so wished, grant entry to heaven/paradise on that very day. There is no problem viz Scripture with that interpretation and no contradiction with any doctrine - anymore than there is a contradiction between Mary’s Immaculate Conception and freedom from Original sin (her redemption) occurring prior to Jesus’ historical death and resurrection.
God’s providence be with you