[MagicRat]

I think it's terrific that a younger person as yourself wants to start off with an intersting older car instead of looking for a Civic and bolting on a wing from a Cessna on the back.

First of all, I agree with Almost Stock.
To add to that, IMO $2500 is a bit high for such a car that needs bodywork. Try offering $1500.
If this car had 2 doors and a V8, it would easily be worth $5000+ in that condition.

These cars are extremely easy to work on, (compared to todays cars).
You can look at any component on the car and easily understand its function, and every component is servicable by the average guy with a little knowledge and basic tools.

You could find used Chiltons or Motor service manuals or books that would cover this car.
Also, old high school auto shop textbooks would give you the basics, too.

IMO the skills you can learn about working on this car can be easily applied to all kinds of different cars and equipment in later years.

Although the cars are simple, some basic service operations arenot seen on newer cars. For example, the car will have a 'points' style mechanical ignition. It's easy to service, once you know what to do, but generally new cars have not used this system in 30 years.

An old Chevy is one of the best cars to restore, because so many parts are easily available.
(Note this is not the case with many other brands, like older Chrysler and AMC sedans)

Local auto parts stores should be able to get mechanical parts, for the engine, brakes etc. Pretty much all the body and interior parts are available on-line from companies like 'Year One' and others.

As for cost of painting, you get what you pay for. A cheapie job can be done for $500, but it looks cheap and will not last for too long.
Anticipate $1500 - 2500 for a decent job.
The key in painting is preparation. Good jobs require more time to get all the panels straignt, eliminate rust, sand out blemishes etc.
If you do a quick study on body work, you will find there are many choices to make, in terms of materials and prep techniques.

Generally, paint and body work to easy to learn. IMO leave the cutting and welding of body panels to an expert, but the sanding and prep can be done by yourself.
Also, possibly, you could learn to paint the car yourself. Many of the most modern paint systems are toxic and dangerous to use, but older style paints (like acrylic enamel) are easier, so long as you have the right equipment.
Your car was painted originally with acrylic laquer which is very easy and forgiving for the beginner to use and learn with.

If you paint the car yourself, avoid a 'metallic' colour. A solid, non-metallic paint is easier to apply and easier to sand and polish out any runs or defects in the paint.
Avoid the colour red if you use an older paint system. Reds seem to fade relatively quickly in such paint systems.

Good luck, and let us know how it goes. Post some pics if you can.