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While I feel the OP's pain in terms of difficulty working with the limitations of AppEngine, what he's not mentioning is the collection of benefits you get from AppEngine over other services. We've found that once you work out a solution to the datastore and request timeout issues, you have a remarkably robust and scalable system for free (or at least out-of-the-box).

With AppEngine, I've never had to migrate a database schema, build a load-balancer, hire a fulltime sysadmin, or even pay for servers that arn't receiving traffic. I don't have to set up a large-scale deployment system, nor spin up a new database server when traffic gets too heavy. AppEngine so far has been remarkably cheap (we're starting to bring in more customers however, so we'll see how long this lasts).

Many of the challenges he mentions come down to thinking about writing a webapp with a longer-term vision in mind. Datastore limitations crop up when you outgrow your first datastore in a standard system; in AppEngine they're properly enumerated and dealt with from day 1. Likewise long-running connections become very tricky to deal with with lots of traffic... this point is a little harder to argue with the recent popularity of asynchronous-io servers, but I think Google is working hard on these limitations. SSL is just annoying; we've had to deal with this by adding an SSL proxy until Google adds SSL support -- but it sounds like Google is pretty close to solving this one (it's been promised by end of year).

Also, AppEngine is written in a very high-level way; should you reach a point where AppEngine no longer makes sense, it is amazingly easy to transition over to another system (as the OP apparently found out; I would give more credit to the design patterns inherent in the AppEngine APIs than 'TDD driven development'). Tornado, webpy, etc have virtually the same interface as AppEngine's webapp framework.

There are definitely tradeoffs when choosing AppEngine as a production backend right now, and its certainly not the right solution for every problem... but for many people, us included, its been a pretty large net benefit for our startup. Google is actively improving the system, and I expect many of these problems will go away in the next 6 months or so.

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