Replying to Manual or Automatic? Whats a good car choice?

So im turning 16 in a few weeks and im looking to get a car in the spring. I live in NY. I need somthing that can handle getting up the mountain.

I was curious about stick shift, it seems really fun once you get the hang of it. Ive driven dirtbikes and atv's before and i undertand the system of it.

Also whats a good car under $5000 for a beginner car? Ive been looking at anything from a 1999 Audi A4 to a 1997 Jeep Cherokee.

Please help me out!