Can't help with estimated cost. Call several well companies. Labor rates vary to much.

Questioon of whether or not you could do it your self are;

How deep is the well?
What type of well pipe do you have, galvanized iron, PVC, or flexible well pipe?
How strong are you physically and what type of equipment or tools do you have?
How much experience do you have doing plumbing work.
What type of connection do you have at the well head and the pipe to the house? Hard piped or pitless adapter?

How long can you be without water as you muddle through this if you do it yourself.