I am interested in upgrading my late 80's system?

This is my first time on the list so I see how little information I supplied. My thinking is to replace my amp first? (guess that is correct) and then speakers. I am very confused by the reviews and since I live in a rural area we have to drive over 3 hours to find a dealer and then I am at their mercy. I listen to classical, Nora Jones,and mild rock. I am past middle age and my budget is around $2,000 total, less if possible. I do appreciate your kind responses and help. I have been away from the game too long to be current.
R

Hi, Again I appreciate the help. Several questions I wanted to answer: size of room 14w X 30 l X 8h. I mainly listen to cds and FM for NPR. I do not have a record player currently I did have an old AR years ago. I still have a large collecion of LP's so may go back to that as a source. My B&W speakers are on stands at the end of the room away from the electronics.
Again very good suggestions and now on to research where to locate items for listening. As stated before not much in the area.
Ray

My response to Cleaneduphippy on my cd player. It is a Magnavox CD 725 5 disc player my wife bought me for my birthday years ago.
I was curious about the Outlaw receiver. I will take a look at the older units for sale as you suggested.
I live in South Dakota north of Sioux Falls about 60 miles, moving recently from the southwest.
Thanks again