First of all due to a major pet peeve of mine, I need to clear something up...
It's STRETCHING... not "gauging".
Gauge refers to the size of the jewelry, stretching is what you do when you put a larger piece of jewelry in. The jewelry are called plugs, eyelets, claws, whatever the type of jewelry, not "gauges".
Now that I got that out of the way.
My opinion of them? Well, I have one inch holes in my earlobes. I don't exactly hate them.

I also have two cartilage piercings in each ear. On top of that, I have my septum pierced now, and am in the process of stretching it to a 6ga.
If you're planning on stretching...
1. Get your ears pierced at a tattoo shop. They'll supply you with quality jewelry (surgical steel), and can help you with the stretching process if need be. It's absolutely unnecessary to have them do the stretching for you, as it's simple to do yourself, but if you don't mind spending the money and are uneasy about stretching yourself, then go for it.
2. Be patient. I won't tell you to wait some set number of weeks, because everyone's body is different. I was able to skip sizes a couple times while stretching and had no problems... then there were a couple times things didn't go so well. For me, 3-4 weeks was usually enough time for me to go up a size (sometimes two sizes). Listen to your body.
3. No blood, no intense pain. At most, all you should feel when stretching a piercing is a slight amount of pressure/discomfort, that should be gone within a day. If you stretch and see blood, or it just hurts a lot once the jewelry is in, that means your piercing isn't ready to be stretched and you should immediately put the previous size of jewelry back in.
4. The larger the size, the more frequent the questions/stares. At smaller sizes, I never really got too many questions or stares from people. Past about half an inch though it became more common. My ears have been at an inch for about three years now, and I've had every question possible asked about my earlobes. Now that my septum is pierced I just get dirty looks mostly. Go figure the piercing that can be hidden by simply flipping the jewelry up into my nose is the one that gets me dirty looks, not the one inch permanent holes in my ears.
5. Be careful with jewelry from places like Hot Topic and Spencers. Believe it or not, some materials are more comfortable in a piercing than others, and mall stores usually sell crap jewelry. It's cheap, which is the only plus side but the materials are cheap too. The worst experience I had with Hot Topic jewelry was when I was at half an inch. The plugs were the ones with the fronts that unscrew, you put the jewelry through, threads and all, and then screw the face on. Well, being cheaply made, the threads messed up after removing them a few times, and the face would screw on crooked and sometimes the threads would lock and I'd have to use pliers to remove it. Well, one time not only did the threads lock up on me, but a bit of my skin got caught in them. After getting the plugs off, and finally replacing them with acrylic plugs, I never bought another piece of jewelry from Hot Topic. Their acrylic and surgical steel stuff is fine, but I'd stay away from everything else, especially eyelets with the screw on faces if they're still selling that garbage. It'll cost you a little more, but buying jewelry online or from your local shop will get you higher quality.
6. Stretching IS permanent past a certain point. What that point is, is different from person to person, but it's pretty safe to say past half an inch, you'll have permanently changed your earlobes. So, always keep that in mind. A plastic surgeon can easily put them back together and make them look like new, but I've read that the procedure runs about $2,000. Some shops have piercers that can sew everything back up and make them look like new as well. Just depends on how comfortable you are with letting a piercer perform what is technically a surgical procedure. Just make sure you're fine with that permanence if you're planning on going big.
That's about all the advice I can give. As far as jobs go, I've always worked odd jobs, and have never had a "proper" job, so I can't really give you advice there. I can say that I have plenty of friends who had no problem getting jobs with earlobes stretched past half an inch. It seems that at least in my area, ear piercings are accepted almost anywhere, no matter the size, or number of piercings. Facial piercings are still pretty taboo amongst mainstream society. Of course, piercings of any size will probably be a problem if you're wanting an office job of some sort. So keep that stuff in mind as well.