Samual,

Welcome to the forum. Sounds like you have a great dream.

For your initial plan, I'd suggest just drawing a line from the east coast to the west coast and leaving it as a dream before spending months of preparation. Detailed preparation will likely be wasted without experience.

I'd suggest doing small legs of the type of travel you want to do and learn from them. This can be as simple as walking to work and school everyday, even in bad weather. Or it can be learning about one facet of travel, such as cooking all your meals on your camp stove.

Before you plan the time for that epic journey across the country, I'd suggest several of a week or two in order to learn what you don't know.

Since you mentioned shoes, I'll address that. Good socks can overcome many of the deficiencies of not so good shoes. I like SmartWool. There are other good brands, also. After you wear out a few pairs of shoes in preparation, you will learn what works best for you.

Money is largely dependent on what food you eat and where you sleep. Whatever you plan, double it.

If you can answer the question "Why do you want to do this?" your reasons probably aren't good enough to finish. I'd suggest planning a trip you HAVE to do.

Have a great trip.