Getting Out Of Homelessness

I don't like being homeless. It sucks, to be honest. I've met some homeless people that seem to enjoy it; they love the lack of responsibilities and the general focus on only their most primary needs like food or shelter. I hate that. Don't get me wrong, I love my life, otherwise I would have off'd myself long ago. However, I don't plan on spending the rest of my life in this state.

I have a plan:

1. Save $100,000
2. Go to South America
3. Start a new life

Of course, there are several details to this plan that I have yet to mention, and a whole lot other details that I may not be able to predict until I have to deal with them.

How to save up to $100,000
As mentioned in a comment below, I may be homeless but I still try to find work every day. When construction work or craigslist gigs fail me, I resort to panhandling (which sucks, horribly). I manged to save around $40,200 in cash during the time I've been homeless; having to pay no rent or utilities for this long does have its benefits. I believe in 3 or 4 years I will be able to hit my $100,000 mark.

That should be the easy part.

How to get to South America

• Independent ground travel: This would be the hardest path to take. It'd involve sneaking across borders (in case I can't enter them legally without having my luggage searched), buying motorcycles to cover greater distances, until reaching my final destination. It would probably be the greatest adventure of my life.
• Take buses and trains: This makes me very nervous; so many things could go wrong, like the bus or train getting robbed or getting in a crash, or someone taking my stuff away if I'm not careful enough.
• Fly: It'd involve getting a temporary residence to get a passport, and then just spending a grand or so on a one-way plane ticket. I'd also have to open a bank account and deposit my money there, since I don't think I can just fly with $100,000 in cash in my carry-on. I have to look more into how I'd go about withdrawing my money once I'm in South America.

How to start a new life in South America
This part I haven't really thought out yet. I just figured that if I can make it there in one piece with $100,000 in my pocket, I'll have an easier time getting back on my feet than if I stayed here. Business ideas so far:

• Open a logistics business: I hear in Peru it's pretty good - but dangerous - business to buy a truck and transport goods around and outside the capital. I have to look more into this, but from what an acquaintance told me I could be looking at $2,500/trip and only one or two high jack/robbery attempts per trip.

I'll keep updating this plan (and thus this post) regularly as my think tank helps me give it shape.