Considering learning Python – idle thought (until something catalyses it)

A friend-of-a-friend asked me this week:

Hi Mike, [mutual friend] referred me to you as a good person to ask: what’s the best way to learn Python for someone like me, whose programming skills are essentially 1990-era (I know Perl and C, but haven’t made the leep to object oriented stuff)? I’d like to leapfrog into the present era, and make web 2.0-ish-looking sites and experiments. Is there a particular web hosting service I should use? Thanks for any advice you might have.

Funny you should ask – I was just wondering this week whether I shouldn’t dive into Python as a quick-and-dirty prototyping language.  I’d fancied myself for years as someone who might be able to reinvent myself as a programmer, and I’ve muddled around with C# and VB for a few years now – but only in short spurts.  Every time I come back to it, I feel like I’m climbing a steep hill all over again.
For some reason, I get the impression that  for folks that are just whipping something together quickly, interpreted scripting languages like Python, Perl or Javascript are easier to deal with – less overhead, less setup, just diving in and getting to the business of making something happen.  I’ve always felt like if I wanted to call myself a coder, that I’d be “cheating” by taking this route, so I never allowed myself the freedom to try this out.  But at the same time, I was never brave/patient enough to mess around with low-level code like C or C++ (who wants to write hundreds of lines of memory-handling routines that managed code gives you for ‘free’?), so I guess I’ve left myself between a rock and hard place – not quite as easy as “just do it” but not really forcing myself to learn the really “worthy” stuff either.
How to learn Python?  An almost-colleague of mine took the leap and blogged his process for going deep – start at the bottom:
I’ve never done it myself, but I trust that Mark is a smart guy who doesn’t muck around for the sake of making himself “look smart” (feel miserable).
For me, forcing myself to learn to code was an exercise in frustrating false starts – until I found a problem I couldn’t solve any way but coding it myself, and a problem that pissed me off enough to keep slogging through failures and dead ends until I got something working.
Web hosting?  No idea.  I know a few big names (AWS, Rackspace, Google Apps) but I have no clue where to get the pre-built infrastructure to just upload .py and let fly.
Is this helpful?  Do you have something specific in mind?  If you’re working on something specific and looking to work loosely with one or a few others, I’d be interested in hearing what it is and whether it fires my “that sucks!” instinct enough to want to contribute/walk alongside.
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