Do I dare say,"It's the nature of the beast".
No matter what we do or try something will go wrong. The toys we enjoy are just that,"toys". The things we have were not made to run or use for prolonged periods of time. It's up to you to maintain conditions as close to ideal as possible.
It was for this reason both of my last prewar layouts used non-connected full loops of track. I never had any operational problems.
MartyE "I am at perfect harmony with my high tech command trains" you should add for now other wise you are sure tempting fate.
James
"how often does stuff malfunction?"
HA-HA-HA!!! Anyone that knows me knows I have the record 
Right now I have my tin-plate Christmas set in for repair and I have a thread on this board asking why an engine quits running.
I OWN this record!
- walt
Me too (at least 90% of the time). We have gotten out of sync in the last month or so, but I'm closing in fast on the gremlins, got 'em right where I want 'em.
If it wasn't for command control (DCS & Legacy) I would not be in the hobby. That and the electronics are as much (or maybe more) fun than the trains. I even want to try DCC someday if my train budget ever exceeds my train purchasing and funding becomes available (is that possible?).
In spite of my shameful wiring mess, for the most part the layout has needed very little maintenance.
Never. My layout is without flaw. Trust me.
Don't have a layout. But the club that I belong to has a rather large layout. It is very well constructed. excellent track-work, beautiful scenery and near perfect wiring. The ONLY problem in the last 10 months was a loss of DCS signal. Cleaning the track resolved that issue.
Therefore, I would say next to never. 
I've never had a failure of track or 'Streets - probably because they are permanently installed, and I solder all joints, jumper and feed every eight to six feet, etc., so there should be not problems.
I run about five locos and six 'Streets cars or truck for about two hours a day, three hundred days per year, and have been doing this for about eight years. The table below shows the amount of each I own and the failure rates I have estimated for my trains and my layout. Your mileage might vary.
Hey, that is what my trains look like when I try to show my grandson which control works a switch while trains are running. He loves it. Also, I hate to admit it, but it has happened more that once. 
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