First off i'm not a pro, but i love to read about sound and inform myself by various information i can get. I really love the world of sound engineering, but i have some question since i need to know others opinion or other knowledge. I write this to know what you guys THINK about it and also to know if there is a way if i'm on the wrong path to hear it. You need too hear the whole story to understand what my questions mean so here i go:

I listened to some pro in local the busyness ad it led me to do a lot of testing regarding the digital world and Analog world. Since top notch analog equipment cost so high, i can't really test those machine, but wanted to test it so i used my imagination. When i listen to music on a wav file i can hear the difference from an MP3 Files. I can hear it so i don't ask why should i mix and use loss-less format (either its wav or flac or whatever...) When i hear a song in a sample of 44k and the same song in 96k, for real i don't hear any difference AT ALL. At those result, for the digital world i put a fresh new vynil (i mean a new album that got out in Vynil not old one) and a CD to hear if there is any difference. *The album i put for the test was "Blackwater Park" From "Opeth"* I'm very puzzled, because a lot of Pro told me there is a HUGE difference between the Vynil and CD in quality of sound. My sound system isn't the cheap one, so i was wondering... Is it me or its just fancy little obsession over analog stuff? And also... if there is a huge difference, what kind of ****ing speaker i need to ****ing hear the difference. With the result i've had... i WANTED more information, more test. In a matters of time i found some way to sound less digital with the sound of my rhythmic guitar and lead guitar. Now thing get messed up. I record my guitar via my Axe Fx, who's supposed to be an effect processor that doesn't sound Digital at all. (as the compagny is claiming) Since i've had the chance to test out real amp and thing like that i know that the Axe Fx doesn't sound EXACTLY like the original, but still sound like a real amp to my ear. When i record my axe fx i almost set it like i set a real amp and feel it. I hear some pro complaining about this piece of hardware, how much it sound digital anyway etc. I'm feeling like my ears are lacking something.

Is it really that obvious when the gear used for a recording is digital? (cause most of the time i can't tell)
What exactly in the sound that make the impression for those people that it sound digital?
Is there a way i can develop my ear to ear it more?