Hope I can answer some of your questions, and welcome to MR.
1. Depends on where in Asia.
Check this page and click where it says "Live Outside the US?" and see what it says for your country.
2. For me $139 would be well worth the switch. I paid $399 for my Kindle and haven't regretted it at all. The screen and adjustable font sizes make all the difference for me.
3. No answer there, I don't download books from the darknet.
4. The keyboard is inactive while reading so there's no problem holding the Kindle from the bottom.
5. The books just download to your default download directory. Calibre is the best ebook management option that I'm aware of.