Welcome!
I'm a n00b myself on the forums but I've been following the bitcoin scene closely the past few months and have decided to jump into the game as well. I've saved up a good chunk of change so I wanted to make sure I had all my ducks in a row before I started so hopefully you can learn from the information I've gathered so far. The one thing you didn't mention in your post was *why* you wanted to buy bitcoins, I am looking to trade so I wanted to make sure I had several sources of coins available.
If you were in my position:
1. Where would you buy from?
It depends on what kind of documents you have and how patient you are. I've tried setting up accounts on several of the major exchanges mentioned already and here is a quick note on each of them so far:
Coinbase - Easy to setup, confirmed my identity answering a few questions that came from my credit report and linked my phone number and bank account without any issue. I am looking to make a sizeable purchase ($10K+) and have read many people saying that their accounts have been flagged as high risk and the transactions held up for long periods of time so I am attempting to get whitelisted before tying up my money. I opened a support ticket to find out what additional documents I can provide so that my transaction won't get flagged as "high risk" but have not gotten a response in over a week. In fact, I usually lurk and don't participate in online discussions but since they haven't responded via the official support channels I registered an account here and will be PM'ing Olaf as soon as I'm out of this spam filter so I can make sure I'm whitelisted and won't have my money in limbo. They are little pricier but the fact that they can make withdrawals from my bank account and I don't have to have my money at risk sitting at their exchange makes them a pretty attractive place to buy and sell from. However, they recently ran out of bitcoins so I'm not sure if they will be a reliable place to purchase from.
BTC-E - Needed drivers license and proof of address. I am signed up for paperless service for my utilities and bills so I opened a support ticket to find out if an electronic copy (pdf) of one of my bills would be sufficient. I heard back the next day and provided via their ticket system (which you have to register at separately from the main site). I had asked in the ticket if there was additional documents needed for a large transfer ($10k+) but they didn't provide any more information and closed the ticket so I'm assuming I'm good to go. They are international so transferring money will require international wire transfer fees which aren't cheap and take several days to process (if everything goes smoothly).
Bitstamp - Needed drivers license and proof of address. They do not accept electronic copies of utility bills but it looks like they accept drivers license and other government issued papers. I scanned a copy of drivers license and voter registration and submitted it it has been pending my verification for over a week, almost two. I opened a support ticket yesterday to see what the delay was but haven't heard anything in 24 hours. They are also international so I face the same issue as BTC-E with fees and time delays.
If you want the coins now and want to avoid all the hassle with documentation I would go with localbitcoins. You pay a premium but you have the coins right then and there and all you need is cash.
2. How much would you buy and wait, buy again?
This entirely depends on why you are buying them. If you are buying them for investment I would buy as many as you can right now. With the senate hearing over and the hearing not turning into a witch trial (plus china buying them up like there's no tomorrow) the price is likely to continue to shoot up and down but it will march towards the top right of the chart. The stock market is hitting all time highs and will come crashing back down once the Fed stops pumping money in every month and when that happens a lot of people will be looking for some other asset to invest in. By that time we'll have high adoption of bitcoin merchants and with the exchanges getting their act together as far as the regulators are concerned it will be a trustworthy investment vehicle that has real world uses.
If you are buying them to use for goods/services only get the coins when you're ready to make the purchase. Otherwise you could wind up using coins that are worth less than you paid for them.
If you just want to try it out and see how the process works I would buy $500, give it a few days to play around with offline wallets, hot wallets, web wallets, mobile apps, paper wallets etc and then once you find a combination that you like drop $1000. If that goes all smooth then you can buy as much as you feel you can risk.
3. Anything else you would do?
I would figure out what your goals are and then make your purchasing strategy based on your goals. If you just want to dip your toes in and have a few coins without hassle I would hit up coinbase or localbitcoins. If you are looking to trade then the sooner you get the process started on the exchanges the better off you will be because based on my experience it takes a lot of time and follow-up.
