Hey buddy! Thanks for the heads up!
I'm totally on your side in that point. Having gone across many borders, I can say they are a strange thing -- mostly, not so much is changing, ethnicity- and landscape-wise. It is, however, a new set of rules and a new sovereignty you might be facing.
In my case, I am doing some research upfront for which visas I'd need, and since I had intended to travel east, I had applied for Iran, Pakistan, and India upfront (the latter needs a paper visa when entering overland). For the bike, there is a customs document which is called "Carnet", issued by your home country, and most countries accept it for temporary import, so that's pretty straightforward. If I do need visas that cannot be obtained on arrival during my travels, I'd just visit the equivalent embassies or consulates.
You've asked about finance -- I have saved for a few years and now, trying to spend little. I'm doing a lot of Counchsurfing and try to avoid expensive activities or places, for that they are quite touristy anyway. Now, I might also generate some pocket money through blogging, but we'll see how that goes. :D :D