I am old so I grew up in a time before o-ring sealed chains. I also spent several years racing off road so I got use to chains that took a beating and got very dirty. I got in the habit of cleaning the chain periodically. I use a special chain cleaning brush and a little WD 40 for cleaning. Then the chain gets wiped cleaned and allowed to dry. After that I use my favorite chain lube, Bel Ray, and let her sit overnight before I ride her again. I ride a lot of back roads, some gravel/dirt and live in an area with its fair share of agriculture so there can be a lot of dust and dirt in the air. I like a clean chain..a clean properly oiled chain is a happy chain and happy chains can last a long time and they share this love with your sprockets.
I don't clean the chain every oiling depending on how they look. I don't do over two oilings without a cleaning however.
I don't log oiling or cleaning but I do keep a mental note of them. Besides, I do them by look and feel of the chain. I do log other service like new tires and services so I have a record of them. I just traded off my 2005 Wee and the new owner has a complete record of all the services, brakes, new tires, brake fluid flushes, cooling system service, battery replacements, etc. on the bike. I like that... Besides, if you keep your bike for a lot of years it really helps to remember when you did certain work. Its easy to forget.
'17 DL 650 Vstrom, Best value ride of all time. (replaced our '05 Wee)
'07 Triumph Tiger 1050 Feel the Power! Culled from the herd...gone but never forgotten.
BMW K1200 GT, Gone but never forgotten
BMW K100 RS, Beautiful German engineering
Husky 250WR, (1986) Last of the real Huskies made in Sweden
Bultaco's ...for those of you who remember....
A long list of so many others.....
Happiness is having a motorcycle with more power than you will ever need.