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advice for small studio for fun and maybe profit? - edited

Note: I have done some searching on this site and found a lot of good information, so I've edited this post to get to more specific questions. I want to be able to do rather minimalist analog recording for singer/songwriter types, jazz combos, and maybe even classical quartets and such. Here is what I have:

Learning from one's mistakes

Do you ever find that only AFTER you are finished with a mix and are in no position to alter it that you begin to find flaws you would have undoubtedly changed? I find that although my recordings and mixes are progressively gaining in quality, there are somemtimes things i hear only AFTER i am in any position to change them. (i.e.

errr, Cool Edit help?

:? I R CONFUSED :?

Ok, I'm a musician and I just bought the Recording program "Cool Edit Pro" because I have friend in the recording business and he recomended it. Well I went out and spent the money on it, and it works fine, but I cant find the option to hear myself in real time as I record (When I sing its crucial that I hear myself). Any and all help is appriciated.