Only sinners can experience jubilee
In the first case, when the Lord called Simon from his occupation, his first realization is that he was sinful. And he really was sinful. He told the Lord he was unworthy of the Lord’s calling. But the Lord called him anyway, showing that His calling of us is not according to our worthiness, but according to His choice, and according to His delight in qualifying the sinful and unqualified ones.
Then next, the Lord cleansed the leper, one who really knew how sinful he was. Following that, He healed a paralytic. But I am impressed that the primary (first) thing He did was actually not to heal him; it was to forgive his sins:
Luke 5:19-20 And since they could not find by what way they might carry him in because of the crowd, they went up onto the housetop and let him down with the cot through the tiles into the midst, in front of Jesus. 20 And seeing their faith, He said, Man, your sins are forgiven you.
This clearly shows that the real significance of his healing from paralysis was that his sins were forgiven, and thus he was able to walk, and “[take] up that upon which he was lying” and enjoy the jubilee as a one released from the captivity of paralysis.
The next case is with Matthew, the despised tax collector. He was one who surely knew he was a sinner, albeit a wealthy, higher class sinner than most. The reason he held a great reception for Jesus was surely because he was in the joy of salvation, having been forgiven his sins. Yet the Pharisees criticized Jesus for eating with the tax collectors and sinners. This shows that while Matthew was in jubilee, they were not. Thus, the Lord stressed that only the sick ones could enjoy jubilee and celebrate with a feast to the Lord; the “healthy” Pharisees who saw no need for forgiveness could not.
This is why the Lord followed in 5:33-35 with His response to the matter of fasting. The disciples of John and the Pharisees fasted, indeed in recognition of their sins. However, the Lord not only brings man to repent of sin, but unlike John and the Pharisees, He forgives men’s sins. This release from sin brings us into jubilee, which causes us to rejoice and not mourn, as long as our bridegroom is with us. (I’m not sure what it means for Him to go away from this viewpoint, since jubilee lasts the entire New Testament age.) This is why Jesus disciples, the leper, the paralytic, and the tax collector could rejoice, whereas those who think they are not that bad cannot.
Moreover, not only does Jesus forgive our sins (bringing us from a negative position to a zero position before God), but He clothes us with Himself as righteousness and fill us inwardly with Himself as the ecstatic new wine of the divine life (bringing us from zero to a positive position before God). Here is a quote from p. 113 of the Life-Study message:
In 5:36-39 the Man-Savior, speaking in parables, goes on to speak of a new garment and new wine. He implies that He is present to cover the despised ones with a new garment and to fill them with new wine. This new garment is Christ as our righteousness to cover us outwardly, and the new wine is Christ as eternal life to fill us inwardly. Only God can cover us with righteousness and fill us with eternal life. These are the deeds of the divine Being. Therefore, in this case also we see the divine attributes expressed in the Man-Savior’s human virtues. He ministered in His human virtues with His divine attributes.
Praise the Lord for my precious Man-Saviour! May I be one who daily repents of my sins, so that I daily enjoy the release of jubilee!