Oh fun! You should have a blast!

I've been twice and am planning my third trip soon.
1. What do I need to do to get started? (planning my trip)
Money! And of course the time off from work helps too.
2. Do you recommend learning some Japanese before I go?
This depends on where you're going. If you're staying in Tokyo with maybe a day trip to Osaka, then no. You don't need to speak any Japanese since most natives speak some English and English is written everywhere. You can get around with no real problems. However, if you're traveling further out into the country, then I highly recommend some common phrases. I went to Mishima and no one understood me. I felt VERY foreign.
We took Japanese/English dictionaries with us and practiced common phrases every time we were in our hotel room or riding on the bullet train. (No kidding.) It never hurts to know a few things.
3. If I dont plan on getting a job (and only staying for 2-3 months) How much money do you think I should bring? (for staying somewhere, food and travel)
Remember first that you can only stay 90 days. That's how long your visitation visa is good for in Japan. After that, you'll have to talk to the US embassy. My father's rule of thumb was always have $100 a day for travel. That doesn't mean you have to carry that much cash. You just have to be able to access that much somehow. They have ATMs just like the US that accept the universal language of VISA.
4. If I want to stay longer (and need a job) where do I go to get one? (what should I go for? - I have no skills to Teach anything LOL)
Can't help you there. Sorry, you have to figure that one out yourself.
5. What do I need to do to find a place to stay at?
Are you talking hotels, etc? Going to a Japanese travel agency is the way to go. You can book a lot of things easier, faster and cheaper than wasting a lot of confusing time on the internet searching or waiting until you're there in person. Before you go, make sure you've looked at a map of Japan. You'll need to know where you want to stay. Tokyo is a big place. Do you want to stay in the city limits of Tokyo or one of the burbs? Remember, Tokyo is more expensive than say Shibuya and everything is only a few minutes away by train.
6. What is the bare minimum I should bring with me? (clothes wise and such)
Think about what time of year it is and what the weather's going to be like. weather.com is a great place to go for international weather. They also have places you can go to do your laundry or have the hotel clean your clothes for a good fee.
7. Should I consult a Travel agent before leaving?
See question 5.
The main thing is think about why you're going. What do you want to see while you're there? Where do you want to go? Everything else should fall into place.
Traveling is fun! Don't let it stress you out.
