This thread deserves a poll 
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Something I never think about, and very rarely have had cause to do - but then these days all of my signal connector contact surfaces are gold plated so don’t suffer from oxidation.
That’s fine as I’m just sharing my experience. It’s useful to note that there isn’t any oxidation with the connections in your system since gold plated connectors are used. I’m not sure if the black or dark coloured grime is dust or oxidation but my system surely showed much improvement after it was removed through cleaning.
Not HiFi but relevant I hope
Back in the day, we had a clinical chemistry analyser, which as it aged regularly had “a moment” the service engineer’s goto cure was reseating the connection on one of the myriad sub-boards after cleaning with 99% IPA. (They were gold plated connections).
Reflecting on it, I have had similar on the odd occasion with computer boards. I must just have been lucky not to have had “a moment” with the hifi…. But then with hifi I guess not many years normally pass without something causing at least disconnection and reconnection of at least some connectors (new components or moving house or rearrangement of gear).
But certainly with nickel or other metal connector surfaces in the past I’ve had occasion to have to clean things up, though the worst is probably when a plug has a dissimilar metal surfaces to the socket surfaces they touch, humid air making in galvanic corrosion a significant risk.
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Avoid any form of cleaner on interconnects, DIN plugs are self cleaning, once a year with a one in-out ‘wipe’ is all thats needed.
For the rest & what I do:
I treat new mains plugs (& sockets) with DeoxIT. I’ve found they stay clean for a number of years when treated from new. Old ‘off colour’ plug pins can be cleaned with wire wool, I avoid ‘brasso’ type cleaners as they leave a deposit & that might not be ideal for good connections. I also have a mix of silver plated plugs, I do DeoxIT these but I have yet to see any sign of anything on these.
I make sure my speaker cable plugs have the same metals as the sockets they connect to - gold to gold with the speakers & nickle to nickle with the amp (I use the 90’ angled Naim plugs). as dissimilar metals will react with each other. I have also DeoxIT’d the speaker plugs, but just the once, I cloth wipe the pins & cotton bud the sockets.
I just ordered another two MCRU silver unswitched double wall sockets, as the old ones were fitted a few years ago and are probably tarnished somewhat inside their jaws and the terminations. At £60 for both and an hour or so fitting, not so bad. I use the kontak audio cleaner and usually order it from amazon or look around the online stores of dealers at £20. If the top is kept screwed tight should last a couple of years.
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Never 
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I should add we do this once a year in spring time when all furniture is moved clear for a deep vacuum & carpet shampoo clean. We call it the big spider & wood louse round up.
Strangely it appears that there’s not a lot of people thinking that’s important to clean the contacts. Probably because Naim doesn’t recommend it….
I think you need to carry out some thorough blind tests before some would believe your findings!
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I know you are joking, because the blind test would consist of cleaning the plugs, listen, then dirt the plugs again, and listen.
What a useful task! 
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I usually don’t do blind tests as they don’t interest me. It’s the same with amp comparisons. Frenchrooster does have a point though, blind tests on Fraim don’t work too. 
The improvements are marked, seriously.
I was kidding😃
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You can test Naim Fraim. If you have 10 boxes, you invite 10 friends. First you ask them to carry in the air each box, in the same time for the 10 persons. You listen. Then they all put back the boxes on the Fraim. Second listen.
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Careful or Richard will moderate this tgread for becoming a proxy discussion of blind testing! (This response tested blid agains no response.)
Being partially-sighted I have specific anxieties about many of the things deemed essential with Naim kit such as rebuilding Fraim or cleaning connections. Patient friend invited me round to their gaff to show me how they do the latter twice a year. Inevitably bent a pin on a DIN 
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We have some contractors working in house downstairs and the mains had to be shut down a few times. While the power was off, a good moment to give the fuse & rod (neutral) from my spur a good clean with some silver polish. Yikes… It was only about 2 years ago but apparently that was too long. Sounded like I’d upgraded something… 
‘Exercising connectors’ is part of routine maintenance in many industries, I do it when I change things about or when a do a thorough clean, perhaps once a year but I’m not going to schedule it in my calendar.
Can’t say that i have ever heard an improvement in sound as a result mind you, neither has my car gone faster or I suspect the MODs’ aeroplanes climbed faster following such planned preventative maintenance, the idea being that they don’t break down quite so often.