Well Well, Oh Well....

Rusty, I can appreciate wanting to do this job on your own,, I am like that also, but like Harry Callahan said, 'a man has got to know his limitations'.
For a job like this at least call in a professional - highly recommended well replacement company and have them give you a worst case estimate.
From that you can make a determination if you still want to do it your self.
And say the pump replacement is going to blow a $1500 dollar hole in your budget. Consider that at any point in time you can walk into your local auto parts store or hardware store and get a part time job, answering questions that you know the answer to, doing things easily that you know how to do and the employer would be glad to have you. At $10.00 per hour net after taxes, work 150 hours and you are back to even financially and you have a new well pump installed.