You have some good points in there but there are some things that aren't quite right also.
1) Yes, oil on the MAF wire is bad
2) No, don't clean with windex, use an electronics part cleaner preferably
3) No, oiling a filter does not necessarily mean that oil will gather on the MAF. It will gather if you overoil your filter
4) No, it is not good to run your filter sans oil. The filter is just a piece of cloth basically, as water seeps into the cloth it will begin to rot away and those fibers will make their way into your engine. Oil keeps the cloth from drying out and rotting.
