Greatly noted and very appreciative for the answers.
Since you guys have enlightened me about the high school level, what is the best way to start out? Obviously I'll be teaching a subject and probably coaching another sport or two throughout the school year... Should I apply for head coaching positions out of college? Or should I stick with the Asst. role? Also, since I want to someday coach at the collegiate level, would it be best to get a 5A or 6A job instead of a 2A or 3A job?
I'm going to say this but I don't mean it as an insult. I actually tell all my assistant coaches this in all our sports (I'm athletic director in case you don't know) that they are never truly ready to be a head coach. I don't care how great the head coach you worked under way - until you have to wear the big shoes you just don't know. Now being under a great head coach does help tremendously but until you have to do it you never know. I worked under three different guys and saw three different types - one great, one not so great and one that was just average. I took something from each one of them but still not the same.
Like I said if your goal is to be a college coach then start the journey NOW when you're young, you (probably) don't have a family to make it difficult to move around, you're not used to having money (trust me this is a big one that people don't realize how much of a factor this plays) and its easier to take the odd jobs to give you flexibility to coach. When I started applying for college jobs I actually did get a sniff from a school which I forgot about in my initial post. You're about to see why I forgot about it. I lived in KY and this job was in Oakland CA so I was going to have to pack up everything I owned and move to the other side of the country. The coach called me up and said he was interested in me and was going to have a phone interview with him and the AD the next day. He coached me up on what he was going to ask and how to answer it. I was super excited because that's a pretty good sign. The phone interview went great and couple days later the coach calls me up and says I got good news and I got bad news. The good news is he was offering me the asst coaching job at such and such university. The bad news is he told me I would be crazy to take the job. That bumfuzzled me because why would you offer the job if you're telling me not to take it? He said the pay was going to be $3000 for the season only, no housing, no other type of job on campus, can't guarantee the job for more than one season and the cost of living there is one of the highest in the nation. It was dumb on my part because I had built a great system, leaving a great paying teaching job, moving away from family to the point I could never afford to visit them and I had a house I owned that who knows when I would be able to sell it. When I applied I was something like 33 years old and I was already at a point in my life it was almost impossible to just start over like this. I asked him to let me think about it a couple of days and I finally told him I appreciated the offer but I just couldn't do it. He understood - it is what it is. That is the only sniff I got out of almost 100 applications.
So if you're going to go the high school route right out of college let me offer this advice. Get on as an assistant at a bigger school. I don't know you but I would bet that you're not ready to be a head coach at this level. Plus, as an AD I wouldn't even interview you because you're so fresh out of college and you have no head coaching experience. This goes back to what I'm saying about the best way to get a college job is to have college on your resume because that attitude is at the high school level.
A bigger school can mirror a small college experience in terms of running a program. Obviously there are differences but it's the closest you'll get. If you go the small school route you have a better chance of getting a HC job but not much better. It will be a much tougher route to build a resume at this level because the depth of talent isn't there. You may get a stud every few years but overall you're going to be coaching guys who typically cannot make it at the college level. Bigger school then typically better depth of talent.
No matter which route you go you need to network like others have posted. Whatever your job in life ends up being more doors are opened by who you know more than what you know. But what you know is what makes you successful after who you know opens the door for you.
This is my opinion and it's based on what I've experienced in my life. Regardless of what avenue you choose I wish you best of luck and hope you get to do what I wanted but realistically will never get to. I wish I had went with a graduate assistant route out of college instead of going high school. I don't regret being a high school teacher / coach and truly love doing it but if I had it to do over I would have went the college route because teaching will always be there.
Hope this helps some.