I guess my biggest hurdle right now is space (aside from money, of course) I think if i had the space i'd buy a nice 302R block or something and start piecing together a motor. It's pretty tough to get an engine in and out of your car in a parkinglot..lol
I basically just learned from reading crap on the internet. before I had my stang, I would decide on a car I wanted and then read up on it. then I'd change my mind and read up on a new car...the stang I didn't read up on first (it was a christmas present). Basically, just read, and ask a lot of questions, even if its something you aren't gonna do....like something you wanna do but then you realize you have no money. oh yeah, and refrain from takin the stang to the shop..that'll make ya learn. when its not runnin and you have no other car to get you to work...you'll fix it
i learned all the machanics of engines and cars from my dad and grandpa, but all the electronic fuel injection stuff i learned from reading, online, books, manuals, whatever. i get bored and i go up to the local barnes and nobles and grab a couple books, read them and then put them back, its cool i learn a lot of **** for free.
Some people can read things and understand while others have to do it hands on. I kinda did both. WHen I was 15 my dad came home and I had the top of my 65's 200 I6 off so I could take it and have a valve job done. Kinda freaked him out but the more you do the more you know.
But know your limitations don't yank apart your daily driver unless you are sure you can get it back together in time for work the next day. So my advice would be to start with some smaller stuff first and work your way up from there.
Also have some knowledgable people in your hip pocket in case you get in trouble and this is a great place to meet those people.