Aging My Own Whiskey

Hello All,

I'm a newb to the whiskey life. I don't drink due to personal reasons, but I love the smell. I have what my family has labelled "the super sniffer". My ability to smell is ridiculously good. I'm guessing that whiskey taste is similar to the smell. The older the whiskey the better/smoother the smell is to me. I recently bought myself a brand new oak barrel. I like to buy the Jack Daniels black label and put it in the barrel to age. Every six months I take a fifth out and insert another. Adding a little each week as it evaporates. Though, I do have a couple of questions that maybe someone could help me with.

1) When I remove the whiskey from the barrel, what is the best bottle top to store it with? Should I use something with a wood cork? I have been using these glass bottles with rubber stoppers. They cork into the bottle like a wooden cork would, but they are made of rubber. It's a pretty tight seal. When I tip the bottle upside down nothing leaks out. My, know it all, friend says that I have to use a wood cork. Is this true?

2) This one is probably most important. My friend, the know it all, said that Jack Daniels wouldn't age in the barrel, no matter what I did or how long I kept it. He ages Evan Williams the same way I age JD. What makes his Evan Williams more "agable" than my JD? Is he right? Will my whiskey not age since it is already aged and then bottled? I can definately smell a difference in the whiskey from the day I put it in from the day I remove it from the barrel. I've never tasted it, but the smell is definately smoother.

I have really enjoyed aging the whiskey and would be sad to hear he is correct. I guess I could always take up baking. At least then I could taste the product. LOL.