To simplify the barrage of informative opinions above, Stylus cleaning can either be a consistent procedure that you do each time you play a new record, or it can be more subjective, largely depending upon now clean and pristine you maintain your record collection.
Records that have gone through a thorough "restoration cleaning process should not require that the process of stylus cleaning be implemented each play.
That being said, I would still recommend the use of one the stylus cleaning devices shown in other blogs above, after approximately 5-6 record plays.
Additionally, even though all of a person's record collection has undergone thorough restoration/cleaning process, the use of a "goat hair" barber brush for the purpose of removing air borne particulates that are usually present in most homes, and always show up every time you take a record out of the storage sleeve, This can be done quickly, via a sweeping process across the entire record grooves before putting the stylus on the record.."Sweep until the particulates are visually gone." This is a definite plus and will also help reduce the need for stylus cleaning procedures.
The need for stylus cleaning should also be noticeable if the record playback shows any distortion, clicks or pops on a formerly clean particulate free recording.
In addition, I have found that experience dealing with this issue in your own environment, is the best teacher to determine how often to clean your stylus.
Of course, don't forget that you records will always need an occasional "quick clean" to maintain their best playback performance.
One final note: I'm certain that you have read manufacturers approximations pertaining to the number of playback hours to expect until a quality diamond stylus is worn to a point of needing replacement. Be aware that these wear approximations are estimated under ideal conditions. DIRT is the biggest villain that will end up greatly reducing the "wear hour" expectation. Replacing a stylus in a high-end MC or even MM cartridge is very expensive. So never forget, " Clean records reduce the need for stylus cleaning and will prolong the life expectancy of your stylus.