Water pressure is created by the pump, so focus your troubleshooting there. Open the well top and with the pressure switch calling for water, look down into the well. There will be a pitless adapter 2-3 feet underground that connects the well to the pipe going to the house. Is the pitless adapter sealing or leaking water? Is there water spraying from the down-pipe below the adapter? Are there wet spots appearing in your yard between the well and house (old galvanized pipes can rust and break)? With the well open, verify that you have the proper voltage available at the well top to operate the pump. Your description of slowly dropping water pressure could be an indication that the pump vanes are simply worn away and not able to create sufficient pressure. You might be replacing the pump.

I went ahead and replaced the pressure switch since it's only like $30, but of course that didn't help :-(

I opened the top (my first time ever doing that!) and removed a ton of insulation (which was a surprise!), and I can see where there's a bolted cover over the well itself and then wires coming from the house. No obvious leaks or wet spots, though:

If I'm right that the electrical wires are coming from the house to turn on the pump, then they should have power, right? I removed the tape from the white and black wires, but I'm not seeing any voltage:

The breaker is definitely on in the main circuit box, unless there's another breaker somewhere that I don't know about?

Following up...

Here's the new pressure switch. The left is incoming from the breaker, so I have the wires on the outside positions; the right is outgoing to the pump, so I have the wires on the inside:

With the breaker on and the switch in the "Auto" position, I measure 245V on the outside, 0 on the inside. I hold it in the "Start" position and I get 245V on the inside.

But when I let off of Start and let it go back to Auto, the inside goes back to 0V. The pressure gauge never moves, even after holding Start for 60 seconds.

I had a helper go to the well pump outside, and she confirmed that when I hold in Start then it gets 245V at the pump (or where the wires connect in the picture in my previous post). And when I let off, it drops to 0.

I checked pressure on the pre-pressurized tank, and it didn't register so it was either at or near 0. I filled it up with an air compressor to 28 (2lbs below the cut-on of the switch) then held the switch to Auto for a minute, but still didn't see any movement on the gauge.

Any other suggestions? With it not sending voltage in the Auto position, for some reason the switch isn't recognizing that the pressure is low and coming on... but it's brand new!

You may have a safety pressure switch; if the pressure goes low because of a pipe break (for instance) the pump switch will shut things off to save damaging the pump. These types of switches must be held 'on' until pressure builds in the system, then the switch will function normally.

If your helper verified 245v at the pump, and no water came out of the well during that time, your pump is probably kaput.

By the way. it looks like you have an old well. That bolted assembly in the top of the well is an old style expansion plug that seals to the pipe casing as the bolts are tightened. To open the well, the myriad hose clamps and piping needs to be removed from the top, then the expansion plug is loosened. At this point, the expansion plug is lifted vertically and all the piping , wires and pump are lifted up an out. If you have solid piping, the whole assembly needs to be lifted, maybe ten feet at a time, and then held while the exposed sections of pipe are removed.

Any suggestion on where that safety switch might be?

I'm guessing that I could remove the pressure switch from the hose, then wire it back in and put it in the Start position (sending 240V back to the pump). Then I would see if it starts shooting water out of the hose, right?

The safety switch is built into the pressure switch itself. See that metal arm on the side for turning the system on or off? There's also a third spring-loaded position where you can manually hold the electrical contacts closed with that arm. Once pressure is building, release that arm and the system is left to cycle automatically.

I would stand next to the bladder tank/pump switch location and watch the pressure gauge. If things are working properly, you will see pressure building in the system via the pressure gauge.

I gotcha... when I was referring to the "Start" position, that's the same thing that you described. I would have to hold it manually, but you could see the contacts closing... that's the only time I was getting voltage at the pump.

Based on everything you've said, then, I'm about 90% sure that I'm going to have to replace the pump :-( I'm NOT looking forward to that one!

Thanks for all the help!

This is honestly so helpful. You need to share this on other platforms.

Pulling a pump can have its problems. If the down piping is metal or solid plastic, the assembly is lifted and then held by clamps such as these as the pipes are unscrewed or cut:

https://americawestdrillingsupply.com/wellpipeclamps.html

Wooden clamp blocks, etc. can also be used. Many hands will help getting the job done. With my solid plastic pipes, I got away without having clamps, but at 15-20 feet of height, the piping would break and come crashing down on us (old solid plastic gets brittle). Luckily no injuries, and only 100' of pipe to pull (!!!), but I didn't know better at the time. If the piping is flexible poly pipe, the assembly can be lifted and withdrawn sideways into the yard.

I installed a new 3-wire pump. The benefit of 3-wire pumps is that the start capacitor for the motor is above ground, so if the capacitor fails, it is easily changeable. Two-wire pumps have the start capacitor inside the pump assembly.

My pump went back in with 100' of flexible poly pipe, brass hose barb adapters and double stainless clamps on each end. Its also a good idea to tie a polyethylene rope to the pump and tie it off at the top of the well; if the piping ever breaks you won't have to pay a well driller to retrieve the pump for you. If anything needs lubricated (pitless adapter, hose barbs, etc.), Crisco is used. Yep, Crisco, right off the grocery store shelves.

Around here (Indiana), it's typically a $500 charge just to open a well. Then parts + more labor $$ to fix things. Either way you go, I just wanted you to be informed. Good luck!

I'm in a heavy internal debate right now... this is going to be way out of my comfort level, and I'd really be doing it myself, which I think is unrealistic. So I talked to a plumber that can come out this evening... OR, I could hook up to municipal water for about $3,000 (which is mainly the cost of digging the trench).

I read that the "average cost to replace a well pump is $1,684, or between $923 and $2,489"

https://www.homeadvisor.com/cost/plumbing/replace-a-well-pump/

The pump alone is $500-650, so if the plumber is going to be over $2,000 then I could spend almost the same money connecting to municipal and not worrying about this happening again :-/

I would take municipal water all day long and 8 ways to Sunday. You have clean water at the turn of a handle. No more losing water when you lose power, no more worrying about ground water contaminants, no worry about well/equipment maintenance, etc.

$3,000 once and done isn't the whole story for hooking up to city water. You're going to have water bills, depending on how much water you use (which you may not think about much now). The water utility may also have a system charge that you've avoided paying up to now. Where I live it's into 5 figures, and is paid over time by adding it to your tax bill for something like 20 years. Meanwhile you don't know how much it would cost to get the pump replaced professionally where you live, you just have generic info from a website.

Also, there may be well and pump companies where you live, and they may be more knowledgeable about pump selection and installation than a general plumber. Replacing the failed pump with an equivalent may not be the best choice.

I decided to stick with the well. The biggest deciding factor between this and municipal was that it was going to be next week before the water company could come out and LOOK at what they'd have to do to hook up! That's a long time to go without water :-/ The $3,000 estimate was 7 years ago, so God only knows what it would be by now.

My local plumber just finished up, charged a mere $370! It took him 2 1/2 hours, so I guess $150 /hour. I rounded up to $400, and that's WAY better than I thought! And well worth it instead of me spending the next 2 days trying to do it myself and messing something up.

The 1hp pump at Lowes (the one the plumber chose) was $475. I also needed 225' of 12-2 pump wire at $1 /ft, and $10 worth of other accessories. So I came out at just over $1,100.