Crank is shot, do I stroke it or not?

If you have to buy a crank I would step up to the stroker. You can do the rear end as you come up with more money. If you don't build the foundation of the motor you want, you will spend more money later when you re do it. Better intake headers, carbs can always be added later.
If your heads are junk I would go with a set of aluminum. If you have to go through a set of used heads and have them ported you are not very far cost wise from new. They are probably what you really want anyway
I think your cam and small carb should be fine for a driver and if you don't abuse it your rear end will last for a while. The more torque at low rpms will help make up for the highway gears at low speeds