Google Earth is your friend, and at the same time, very much your enemy, in this venture.
I say only jump any border if you have some small, well planned, and highly low key, low risk task to accomplish there, before heading right back. Never jump a border to be a hero, and never jump one looking to stay, or you run a really good risk of eventually getting nailed. It's very hard to live somewhere for any length of time where you don't have valid paperwork to be -- just think of all times you take for granted when you need to show ID or fill out official forms, in order to do a lot of the basic things for surviving in society. It's really a law of the jungle kind of arrangement for illegal immigrants anywhere.