Replace pitless or not?

We recently had to replace wiring on our well (drilled in 1989) and when they were putting everything back together the "O" ring did not seal properly. A small amount of water spurts out when big water users are on (like hoses). They tried sanding the area (there was a small pit on one side, from wear I guess) and replacing the "O" ring but that didn't solve the problem. Then they put a new pitless on but of course it wasn't an exact match and the plumbers actually used a hammer to wedge it down into place. (We won't be using their company again.)

The short of it is, there is still a small leak where the pitless is. It spurts a little out a few mintues after the water is turned on and then stops spurting out afterwards. The pipe is galvanized and would be a real job to replace the pitless connection itself.

So is the leak a big enough deal to warrant paying for replacement of the pitless connection, OR is the long term effects of it not a big enough deal to put the time and money into fixing?

Thanks for any help!