First the system should be tighter than a frogs skin. Get the ducks in a row and make sure there's not any bad faucets in the house or Bossie has her tongue caught in the water dispenser out in the barn.
Now air compresses better than water. It's an important thing. Rather too much than too little. But too much out either extends the cycle time or increases it's frequency of cycle. So if there's not enough air in the tank, I would cut the power to the pump and close the shutoff valve after the pump before the tank before draining the tank. That's before and not after the tank. To help draining the tank, I would open a faucet someplace else in the house for the tank to drain faster. When the tank is drained, remove the screens from the ends of any faucets temporarilly that were opened as when restoring pressure may loosen sediment or other grundo in the line and clog them up. Shut off the faucets. Restore power to the pump and only then open the valve between there and the pressure tank. Then when the system has got it's full pressure and the pump has shut off, open the faucets that were opened priviously one at a time till steady flow comes out and shut them off individually after that flow has been restored.You may get some rust and such but don't fret. When the water clears, shut the faucet off. Do this faucet by faucet as necessary. If things aren't working slicker than snake snot on wet grass now, (which means as they should and then you can put your screens back on) then I would look to the Square D Switch.
Now if you don't want to put out a couple bucks for a new switch or know how to diagnose the electronics for it, call a pro now.
You could have a clogged nipple on the well head.
If I'm not mistaken, the well pros come out with a hand pump that looks alot like the one my grandma used for her soft water cistern in Minn. as early as '65. With that, they can tell if the well is clogged by the pressure they have to use. After that they may use chemical acid chrystal to restore the flow after a 24 hour waiting period for the stuff to work. If that doesn't work, well ...do you dig it?
Now dollars to donuts, you're never going to go to this length. Air has a way of mixing with water over time and once in a while, you just got to cut the tank off and drain the rust and lime and restore the proper amount of air in the system for the thing to work right. Same thing for the water heater. When you have a well, you may have calcium deposits that, if given time to collect, will suck the service life out of it and waste gas as well. A little water should be drained out of these once a month till it runs clear.
You don't have to do this to the pressure tank as often, but this is well water. There's reasons why city folk have to take vitamin supplements and farmers don't!
And one final thing. To coin a phrase that was used in one of the privious threads, ghetto hookups. When you mix copper pipe and galvanized pipe, you have to have what's called a dielectric union between them. This breaks the electrical connection. Water is an acid. When Zinc (as in galvanized pipe) and copper are combined in an acid, there's electrolysis.
Prior to when some suburbs in this neck of the woods changed from municipal wells to lake water, some developers built some places pretty fast, and not saying they do or don't now if you catch my drift. A twelve story condo building had two inch pipes with a half inch for source flow inside. And there's alot of places in the city that have evolved band-aids to deal with that problem despite the soft water lake source they've have for a dogs age.
And don't feel overwhelmed by all this. I went to an Ace Hardware store and asked a part time kid (after he said in typical Radio Shack style, "Can I help you?") for a dielectric union to go between half inch copper to a three quarter inch galvanized nipple. It's like anatomy if you don't go to school for it. You learn.