Redhotpengy,
Currently, much of my work comes from two companies that send me work. The benefit is that I've built up a relationship with them and they send me work. The negative is that I have to do about 20 jobs a month to hit my income target. This doesn't allow the high quality work I desire. But it adds a lot of variety. I have a few of my own clients, and the ideal is to have 100% client work. That pays better and is more on point.
The college program in the media arts sounds cool. I am glad I went to college. No regrets. I am not a believer in student loans though. I worked full time and went to school part time and paid cash. Having huge student loans will cause problems later. A fellow friend from our college has over $100k of student loans. I have none. He went full time, I went part time. He graduated, and I didn't, but in this field it doesn't matter. Your portfolio is what sells, not your degree. He is crazy talented with motion gfx, but his monthly student loan payment is something like $800 - $1,000 a month. Stupid.
If you are going to do the college program I would try to work full time and pay for it as you go. Unless your parents are paying for it. If you graduate with no loans you'll have more options and more creative freedom.
Gear wise, I shoot with a JVC HD110 with accessories. I've put close to 700 hours on it and am super bored with it. I definitely want to play with DSLR's and primes. I also have an ARRI light kit, and some Chimera soft lights along with some decent audio gear. I am basically one man band. I heard someone say once that a videographer that doesn't know lighting can earn $50,000, but a videographer that knows lighting can earn $100,000. Lighting is one of my favorite subjects. Cinematography is super interesting to me. I want to get a DSLR and play! Got a wife and two kids, so it is not as easy to buy gear. That is the challenge with this industry. There will ALWAYS be more toys one can buy.
The 60D is a solid camera and you have some nice lenses. You can do good work with that. Do you have audio gear?
Twenty jobs a month? Wow, that's a lot. Is there always a lot of pressure to get them done? If you don't mind sharing, what is your income target?
Ah yes, of course. However, I live in Canada so the price is much lower (I'd say total $40,000 for 4 years). It's still a lot, but thankfully my parents have money saved for this. I'll still have to help them out, of course.
You're definitely spot on when it comes to the portfolio; that's the only thing that really shows you can make a film. No matter what school you go to, if your portfolio sucks you'll get nowhere.
DSLRs are very fun to film with. In terms of controlling the camera, it feels somewhat like you're shooting on film; primes, adjusting shutter speed, manual focusing, no smoothing (depends on the lens), etc. What's really cool is that a hacking project called Magic Lantern made a modification that allows you to film raw DNGs (digital negatives). The results are spectacular; on a 5D Mark iii, you can shoot raw 4k! However, I can probably film about less than 5 seconds of raw uncompressed 1728p video; about 15-20 seconds worth of 720p, and this is on a class 10 card. Still, raw 720p looks better than compressed 1080p.
As for audio gear, I'm pretty limited. I only have a rode shotgun mic. The last narrative I shot, I actually did all the audio in post, and it wasn't too bad! Mind you, I was going for a Fellini-esque style...
I'm also curious about cinematography; the saying you have is definitely true. Lighting is key.
Do you have a reel I could see?