I'd pay close attention to Grizzly10 above. It's obvious that what you're describing is theoretically possible.....but it's a rare individual who could actually pull it off, whether possible or not. Rarer still: the individual who could sustain it over time. Maybe you're that person, but the overwhelming majority of us are not.

I'm not, for example. I've spent more than that on every extended trip I've ever taken, even those without a vehicle. With a bike there are lots of added expenses; with a Mog, more so. How will you get the Mog from India onwards? Not via China, and not shipping it to SE Asia or Australia either on that sort of budget. You're really talking about a trip through Europe and the Stans into India then?

I'd pay less attention to those who say that's their dream too, therefore you should do it (even though they can't). That's not the voice of experience in any sense; it's the voice of people who want you to live out their dreams. You've got enough on your plate figuring out how to live out your own dreams.

On the other hand if you've got a backup plan--also known as an escape hatch--then why not try? Throwing off a secure job and situation in order to travel for a while is not as big a deal as it sometimes seems--I've done it several times. But you might want to find a way to dip your toe in the water without risking a whole lot before you fully commit.

I'd think carefully about cutting things too close with your rental income: as indicated, things sometimes go off the rails in a hurry if you're not there to keep tabs on it. I've traveled all over the world relying on rental income, with and without motorcycles; when it works, it's great. The idea is to have a plan for what to do when it all falls apart.

Hope that's helpful. Good luck!

Mark