Volvo farmer and amatuer electrician.

Volvo Farmer

I assume you have one inch pipe in the well.  Measure the distance from the top of the well casing to the pitless adapter.  Add one foot and get a piece of steel pipe that length, one tee, and two 2ft pieces of pipe. Make a tee, screw the free end into the pitless adapter, and lift the pipe off of the adapter.  At this point you know how much weight you're dealing with.  If you have iron pipe, it's a lot.  I installed the pump at my first house using iron pipe, but I never tried to raise it.  It's heavy.  Plastic's a lot lighter.  You may want to build a tripod and get or buy a decent hand winch.  I used the winch off of my sawmill.  Don't cut corners.  There's too much at stake.  You will also probably want some way to clamp the pipe.  Humans tend to make mistakes and let go at the wrong time.  I watched a 24 inch pipe wrench dive into the well once (my mistake).

Too late now but in the future don't FILE them!  That removes metal.  (Use a contact burnishing tool.  It looks like a little file but it just moves the metal around rather than taking it off.)

Meanwhile, reopen the switch and clean off any oil you left with alcohol or acetone.  (Beware fire risk.)

As for jumping across the legs for 220-240v I get a 1 :(   Darned meter is a digital and not reading that right! I also had the power company out to check power (different reason) and at the pole his meter showed 240 jumpping the legs, mine was still a one so I know that's the metter. Time for a new one??

Sounds like the meter was set to a scale where 120V was within bounds but 240 volt was an overload - so it "pegged" and read "1".  Check whether you have a higher voltage scale.

If you don't you can make a voltage divider out of a couple resistors to get it down to where the meter can read it.  Or just make a trip to your radio shack or whatever for an inexpensive new one that CAN read that high.  Analog meters are good for house voltages, too.  They average out screwy waveforms rather than getting confused.

Haven't opened the well yet. I am thinking maybe a leak in the well/pipe somewhere. We have been getting alot of rust out the taps for awhile. Just changed the hot water tank element, tank had lots of rust sitting in it. Far to much to be from the tank itself, would be leaking bad if it were. Only other metal would be the well pipe, everything else is plastic. But a heavy steel pipe rusting out in 5-6 years??

It's called "galvanic corrosion".  If you have even a tiny average DC current feeding the pipe (including a potential difference between the ground at the top and bottom of the well, or unbalanced load from a light-dimmer that's half-cycling), and part of the pipe ends up a bit positive relative to the water around it, you set up an electroplating cell that can rip the metal out of the pipe in a matter of weeks.  If your pipe is still usable I'd add a sacrificial annode near the wellhead to give it a little help staying negative.

Galvanization consists of plating a little sacrificial zinc on the pipe.  After it has sacrificed itself (typically due to well water with a pH far from the neutral 7) the pipe starts to rot.  Then you get a rapid increase in rust observed in the water as the pipe starts to go.

If you have been seeing rust all along I'd suspect it was from the well rather than the pipe going.

Regardless, if you have to pull up the pump for any reason you probably want to replace the pipe with PVC while you have it out.  (Tape the wiring to the pipe twice per 20'ish pipe section using tape intended for the purpose on the way back in.  DON'T tape the safety line.)

Only reason I haven't opened it is a worry of dropping the pump! Not something I've ever done before. Sounds easy enough, but getting any help would be the hard part.

The safety line should be fastened to the pipe fitting, not the well cap.  You can pull the cap without worrying about dropping the pump.

Pull the cap and run a weighted string down to check the water depth before worrying about whether the pump/plumbing is working.  Your well might be going dry of filling up with dirt.

As for the electric, I have the Grid power ran to the well pump house then to the house.

If you ever want to go off grid look for a "soft start" controller for the motor.  This will ease the peak load on your inverter.

SO the breaker is at the well basically. I did that for several reasons, one I can shut power to the house off and still have a well, and also when the house is off grid only the well will need the grid still.

Also required by some codes.  It lets the firemen turn off the house and still have the well pump running for a water source.

Not that it really matters, since a household well pump only provides a "drop in the bucket" for a firehose.  B-)  What you really need, if you don't have a handy lake or stream, is a big storage tank or a "firepond" that you filled with water BEFORE your house or field caught fire.  Consult your local fire marshal for sizing.  If you have land uphill from your house you can put it there and let it also provide pressure and water storage for your house.

So what's the danger of dropping a pump into the well if I screw up? And if that occured any way to get it out or is the well ruined??

Should be possible to fish it out even if you drop it.  It's just a lot harder than if you don't.  B-)

I am normally the do it myself type, just a bit worried about dropping 300' of steel pipe and pump and needing a new $5000 well!! I do have 300' 2" heavy wall steel pipe laying in the yard I could use part to build a boom or such. Have a cheap 12v winch, but power in only. Will hold the load but no way to lower it bu release it and let it free spin though I could probably rig something up to lower. How heavy is that going to be??

Before doing it yourself, why don't you get an estimate from your local well driller for pulling the pump, checking it and the well out, and replacing the galvanized pipe with PVC?  He has the special equipment for doing it easily and quickly.  (Including the winch/derrick on the back of his truck, special hardware to grip the pipe, an air pump to clean out the well if it's full of dirt, and non-toxic waterproof electrical tape he bought by the case.)  He buys pipe wholesale and sells it to you retail, while you probably have to buy it retail no matter where you get it, so you're even there unless you have a deal with the plumbing outlet.  Once you've seen it done you'll be able to make an informed decision on whether to do-it-yourself or hire his service if anything ever goes wrong again in the future.