I like Python because it forces people to write code that is relatively easy to follow. Hell is other people's code. Python will help get rid of some bad habits you may have picked up from PHP (though Ruby might do this as well). As far as jobs go, I've seen far more Ruby web development jobs than Python ones, especially among startups, so it's definitely a language I'll be learning soon, but I think I'll still prefer Python.
Another plus for Python is that Django's documentation is excellent and free. From what I've heard, you have to pay for all the good Ruby books, and printed documentation ages poorly. Django's documentation is religiously updated to reflect new changes.
I host my sites on a Linode VPS. They did obliterate my VPS when my credit card expired which would normally make me never use them again, but I didn't actually lose any data and they're cheap. You get what you pay for. For DNS, which you'll need if you host off of GoDaddy, I use ZoneEdit, which is free for your first five domains. I've used up my five free ones, and when I removed one domain so I could add a new one, they told me that technically, only the first five domains are free, but they let it slide anyway. I'll definitely be sticking with them.