Repetition does make a difference in how much reparation for that sin is required and how hard it is to break the habit.
Catechism
1459 Many sins wrong our neighbor. One must do what is possible in order to repair the harm (e.g., return stolen goods, restore the reputation of someone slandered, pay compensation for injuries). Simple justice requires as much. But sin also injures and weakens the sinner himself, as well as his relationships with God and neighbor. Absolution takes away sin, but it does not remedy all the disorders sin has caused.62 Raised up from sin, the sinner must still recover his full spiritual health by doing something more to make amends for the sin: he must “make satisfaction for” or “expiate” his sins. This satisfaction is also called “penance.”
1473 The forgiveness of sin and restoration of communion with God entail the remission of the eternal punishment of sin, but temporal punishment of sin remains. While patiently bearing sufferings and trials of all kinds and, when the day comes, serenely facing death, the Christian must strive to accept this temporal punishment of sin as a grace. He should strive by works of mercy and charity, as well as by prayer and the various practices of penance, to put off completely the “old man” and to put on the "new man."85
**1865 **Sin creates a proclivity to sin; it engenders vice by repetition of the same acts. This results in perverse inclinations which cloud conscience and corrupt the concrete judgment of good and evil. Thus sin tends to reproduce itself and reinforce itself, but it cannot destroy the moral sense at its root.
1876 The repetition of sins - even venial ones - engenders vices, among which are the capital sins.