"One thing I have figured out in the past 2 days is that I believe my pressure tank is shot. It is not holding air for more than a month or so. So that needs to be replaced regardless. I guess I will start saving for a new pump just to be safe."

Unless you have a bladder type tank, this would be normal. Water absorbs air. All you need is one of those air injector systems that adds a little bit of air every time the pump runs. They only cost a couple of dollars.

As for the pump, if you had a new one installed recently, there shouldn't be anything wrong with it. Mine is around 40 years old and still going strong. Two things you can do, one is, when the tank has a proper air charge, is to time how long it takes the pump to refill the tank from the low pressure to the high pressure settings on the controller. Your well driller should be able to tell if the time is about right for the depth of the well.

If you know someone with a clamp on ammeter, then measure the run current to see if that is consistent with the pump motor specs. If the pump is fairly new and it is drawing too much current or taking too long to fill, it may have a manufacturing defect or it got something stuck in the pump vanes when it was first installed.