What's the ultimate goal for this property? Are you building in the spring?

I'd say just get it disconnected and buried. Then once the building has started you get it reconnected and installed in the proper place.

You don't need water over the winter.

Originally we were planning to build, but much deeper on the lot. However, that plan has been put on hold. We continue to "improve" the land by planting trees, etc. It is 5 acres and we enjoy working on it. Not sure if we will ever build or not. We want to keep water so we have it to water newly planted trees. We are hesitant to pay $2,000 for a pit as it will be harder to recover costs if we continue to sink $$$ into the lot. I get the irony of this as we spend $$ on trees! No need for water during the winter.

Get rid of the water line and just haul water if you'd like to continue planting trees.

That is a bit easier said than done as we have planted about 75 trees thus far. Our summers are very hot and dry, so I need to water fairly often the first couple years. Could I try putting a small tube into the pipe and using a hand pump to push air into the pipe which would force water out? I only need to clear out the first 48" of pipe.

Are you talking about the section from the meter to wherever the spigot is? And you're going to be disconnecting it from the meter?

Sure ... you can blow out the whole pipe if both ends are open. It may even just drain itself if there's a slope. That's what you do with houses/cottages that get closed up for the winter. Open up the drain spigot and blow compressed air in the other end.

No, I am talking about leaving the pipe from the water main (deep underground at the street) to where it comes out of the ground (on our lot) . This copper pipe attaches to the meter and then a faucet. I would remove the faucet and the meter, leaving just the copper pipe that goes to the main. I can't blow out as far end isn't open, but attached to the main (water will be shut off at main by the city). The slope would be back towards the main as that is deep under the street.

You can't remove the meter. The city would have to do that. And I'm sure they'd take care of whatever needs to be done. They own everything up to and including the meter.

Are they really willing to come and shut off and on and reinstall the meter every spring/fall? I think they'll require you to do something more permanent. So either get it done properly (your $2000 option) or get it turned off permanently. They may have set this up for you initially because it was just going to be a temporary situation since you were going to be building.

Actually, now that I think about it, the main shut off may have an automatic drain that gets opened when the valve is shut off.

Check with your utility company. You may be worrying about something that isn't an issue.

good point on the drain....I will check. Yes, I actually spoke with the city before connecting the meter to the exterior pipe. I was surprised, but they said they will turn it on/off in the spring and fall for $35 a pop. They have seen it as is as they needed to come and put a remote reader on it. I will check with city and see about the automatic drain. Thanks!