I've thought a lot about this topic over the last year or so. I think this part the game has become a "new school" evolution. Not that it ever wasn't before, but now that the game has changed and accessibility to pro photographers is so much easier. There is also a lot of free information available online where if people dig enough they can find a lot. I'm finding a lot of successful photographers that learned on their own, and had a college education in something not related to photography. That said, there are things that you will never learn online. A lot of learning comes from observing, and being around the environment that you aspire to be in. Having access to that is much more difficult.
To really get going in this industry you have to learn somehow whether that's going to college for it, taking some sort of course like the workshops in Santa Fe, workshops from other photographers that are teaching. So basically you have to pay to play. Education costs money in any industry or field. It's part of the sacrifice that comes with learning a craft. The essential knowledge will cost you somehow whether it's time or money.
In my opinion the best way to learn is with working professionals. It's been the best way for me to learn. Taking a workshop from someone who's work or business that you admire when they offer one. I did this a few years ago when my friend Stephanie Rausser taught a class at Santa Fe. It cost me a few grand, but in the end, I learned a lot through conversation with them during and now after the workshop. Was it worth it? Of course. A lot of times, photographers of that caliber rarely teach because the commercial world as I've come to learn is extremely crazy and last minute. You can get a call one day and leave 3 days later to shoot it, so it's hard to plan for. Most are focused on being photographers, which is time consuming in it's own right. Taking a workshop is as easy as finding them, signing up for them, and paying for them. They aren't ever cheap.
Another avenue is interning for a photographer, which if you have more time and less money this is a great way. Interning is a great way, and probably a better way because you get to spend time with that photographer. You get exposed to a real working environment which is valuable. In turn for this you're giving your time. Who said picking someones brain was free? Think of all the time, years, and sacrifice that individual has put in to get to where they are at. Think of how valuable that knowledge is. That changes the perspective of "working for free" It now becomes a trade of time and hard work for knowledge, exposure, and experience.
That said, what you get out of it is all what you put into it. The harder you work for that person with a great attitude, and the more questions you ask, the more you will learn. This is with either case of taking workshops, or interning. The move you give, the more you will get back. If you give without expecting in return, the reward is usually much more. Most photographers are willing to share things when people are giving back to them.
Again back to the new school era where there are many aspiring photographers, how do you stand out? How do you get in? How do you get selected for an internship? This is the tricky part. Here are a few thoughts:
Great Attitude: This is the most important asset to anything. Being willing to work hard and happily will get you far. Being energetic and excited to help doing whatever it may be. Even sweeping floors and cleaning toilets.
Have something to offer: A lot of bigger photographers get hit up all the time for internships, assisting, brain picking, etc. Have something to offer, even if that is paying for a meal. It's a nice gesture in trade for their time. More than likely if they can spare the time to even meet with you, you'll learn something. Don't come with an attitude of "tell me everything you know" AKA don't be a leach.
Special Skills: Having a skill that is outside the photography realm can be valuable. If the photographer needs something done in the office, or other types of things that you may have a skill with. Offer that up. It may be a way in the door.
Be Responsible: Being someone the photographer can trust, especially getting a task done well and on time.
Be COOL: I mean this in the personality department. Be someone fun, and excited to learn. Bring something to the table. Be a pleasure to be around, and I'm sure you'll get asked back.
Bring Value: This is semi covered above, but always think of value that you can bring to the team and the photographer. Think ahead of them. The more you give, the more you will receive. That is just a law of nature.
Timing and opportunity: Remember a lot of getting an internship or even the chance to meet with a photographer comes down to timing and opportunity. Be patient.
Jeff Holt has been a great example of this all of these qualities, and in turn he has learned so much. He's been a huge asset to me and has helped me out in so many ways. He approached me in the beginning willing to sweep my floors. He offered his great attitude and acquired skills over the years to bring value. He comes with a giving attitude, and receives greatly for it. What all has he learned? That may be a more specific question for him to answer.
To sum it up, Knowledge has become the currency of our era. As with most things these days you have to pay in some way to gain that knowledge. The more you put in and give, the more you will learn and receive.