I would recommend buying a toolkit so you have everything you'll ever need. Buying tools as you go costs more, and it's very satisfying to pull out your bicycle toolkit and have everything you need right there in front of you. I have this kit from nashbar:
http://www.nashbar.com/bikes/Product_10053_10052_524452_-1___if that link doesn't work, it's the Nashbar Essential Tool Kit. It's $50. I think the $150 one is basically the same but with nicer handles. (though ball-end allen wrenches can be super-handy some times)
I've had it for about 10 years and used every tool in it at some point. (And mine is an older version, with a few relic tools that are missing from this version)
I also have a bike stand (~$150) and a truing stand (~$50?). Eventually you'll get to a point where you're like, yep, I need those, but you can get by without them for a long time.
I only replace tubes when they don't hold air (but always carry a spare), and for emergencies I pack a multi-tool, patch kit, and tiny pump.
And remember to
clean your chain before you lube it. I do that maybe twice a year on my commuter (short commute), and every 3 or 4 rides on my mountain bike.
Zinn and the Art of Mountain/Road Bike Maintenance is a great book to have to read about various things like tuning. It can be a pain in the ass because it talks about the 10 billion types of everything you can have (disc brakes, hydraulic disc brakes, mechanical disc brakes, V-brakes), but it's still helpful.
I don't have a favorite youtube channel, I just google everything.
In terms of wisdom and advice - if something is really stuck, don't push really hard without noting where you're going to end up if it suddenly gives. it's very easy to really mess up your knuckles. Bike maintenance is very difficult in my opinion. I'm sure a lot of people will disagree with me, but I do just about everything, I repair a lot of stuff on my car that most people wouldn't, I repair most of the stuff in my house, I'm an engineer in RL, and I think bike maintenance is extremely challenging. But that doesn't mean you should pay someone else to do it, it just means you should be super proud of yourself any time your bike is in better condition after you work on it than when you started.