Hey OP,
Python is a good choice, especially for automation related tasks. Its a great language really, the REPL alone (while not the best REPL around) will allow you to prototype your code rapidly and develop in an interactive environment. Learning resources wise, there are plenty. Have a look at my previous posts, think I've posted something on learning python.
So good choice OP, keep at it and you'll succeed. Feel free to drop me a message if you need help with something.
Java is such an unforgiving language. Python is a great language to learn for newbies. It's not unnecessarily punishing and touches on all major points of beginning to think like an object oriented programmer.
I have seen Java discourage, frustrate, and completely turn new hopeful coders away from learning programming. I mean, think about JQuery. It's a son-of-a-bitch to type all that syntax by hand. Especially in an unforgiving and super strict language.
I strongly recommend NOT going with anything Java for your first language. There are really only 2 Excellent choices here. Python and Ruby on Rails. The amount of time saved by spending it learning how to think like a programmer and not how the hell to satisfy a strict set of syntactical rules is by FAR more valuable in the end. A good coder is one who thinks with good coding methodologies. Not one who knows the semantics of a particular programming language or even a substantially different derivative of the same damn language.
Learn to think like a programmer. Then worry about typing like you will be forced to.
I'm not really sure what jQuery has to do with Java... I agree on Java's verbosity and I'd also advice beginners to stay away from Java (albeit due to other reasons than the ones you've mentioned). I do think that the language is a lot more forgiving than you describe here (implicit type conversion, dynamic array assignment, etc). Sure the syntax suck, I agree, but then thats really a love/hate type of thing. Lots of people absolutely hate Python's forced indentation syntax (I'm not one of them btw).
The other thing is. The JVM is fast. Probably one of the greatest pieces of computing architecture around, seriously. It does some magical stuff. Much, much faster than Python or Ruby. Another thing is, concurrent programming is very easy in Java. Python and Ruby don't offer the same primitives... (Pythons concurrency model sucks big time at that).
So yeah, there are always negatives and positives in any language. My advice to OP would be to just stick with something for a while until you becom very comfortable in that. Afterwards, go and explore other languages. Don't stick to the Cs and the Java's either, there are many beautiful languages around, just be open to other paradigms.