[snewe]

Important caveat:

"I’m not kidding when I say that I spent probably more than 24 total hours in the past three weeks having a blast on this thing creating itineraries, checking mileage, and figuring out where the heck I could go without going over the limit."

[salvadors]

The "having a blast" part is important. I've built similar trips myself, and playing with all these tools, finding interesting routes etc can be great fun (like discovering a way to get from Kyrgyzstan to Austria via Ethiopia and Jordan at no additional cost). It's a form of hacking that can be just as addictive as any other, and has the added benefit of helping you see lots of the world cheaply!