Jason
I am sympathetic to your desire to move ahead rapidly, but I must agree with the many comments saying that the only way to progress at all is to be solid in the preliminary subjects.
Math is progressive. Calculus builds on trigonometry, geometry, and elementary algebra, and they all build on arithmetic. If you do not understand algebra and trigonometry (and some geometry) thoroughly, calculus is a bunch of arbitrary rules, and solving word problems is impossible because the principles involved are all mixed up with algebra, geometry, and trig.
I do not agree, however, that you necessarily need to take umpteen courses. You seem willing to work very hard on your own. What you absolutely need to do is to determine what you do not know. Get a beginning algebra text out of the library and do the exercises that have answers supplied, including the word problems. (I like Khan Academy, but I think that it concentrates too heavily on mechanics at the expense of applying math to problems. That is what word problems are for.)
If you know beginning algebra well, you will race through such a text. Furthermore, make sure you understand the logic behind the procedures. It is not enough to know how to do something. You need to know why to do that something and not some other thing. If you find that there is some aspect of beginning algebra that you do not understand (because you cannot get correct answers on the problems that are answered in the answer key), start doing the other exercises and come here to have your work checked. Given your willingness to work and your apparent intelligence, I suspect that you can review and fully master a first year high school course in elementary algebra in a few weeks. Then do the same with the second year of high school algebra. This is usually called intermediate algebra although it is just a continuation of elementary algebra. Again I suspect that you can review and master this topic in a few weeks on your own. Back when I went to school, they had no course called pre-calculus. Certainly the people who discovered and elaborated calculus in the 17th and 18th centuries had nothing but algebra, geometry, and trigonometry to rely on. So I have no idea whether or not a modern pre-calculus course is particularly helpful to someone who has a solid knowledge of elementary algebra and trig and analytic geometry. Probably teachers of calculus have discovered that the average high school has not taught algebra and trig solidly enough to prepare most students for calculus, and pre-calculus is a way for colleges to remediate the defects of the high schools. (This may be unfair. In my high school, I took a course in my junior year that included trig, three-dimensional Euclidean geometry, some beginning set theory, and some beginning number theory. Except for the trig, I do not remember this grab-bag of a course as being particularly pertinent to calculus, which I studied in my senior year. Of course, students may not be the best judge of the logic behind a curriculum.)
In short, I do not think that you personally need to take four or five courses before you can study calculus with a high likelihood of success. I think that because I think you personally can master the preliminary subjects with the help of some good texts, this site, and some of the resources on the web. But you will never understand calculus without having previously mastered algebra, analytic geometry, and trigonometry.