This is from experience learning, continuing to learn, and writing a relatively simple application in Rails.

1) Learning Curve

Rails is deceptively simple. The tutorials, videos, and books all demonstrate how quick you can get a working (if ugly) application, but these really just scratch the surface. They tend to heavily rely on code generation and "scaffolding" which admittedly is a good tool when learning but quickly outlives its usefulness.

Make no mistake, Rails is hard to master. Once you get past the very basics (more on this later) you will run headlong into a wall if you need to do more than the extremely simplistic "demo app" functionality that you see touted. You can get by with a basic knowledge of Ruby while learning, but you quickly need to pick up Ruby or you'll be left high and dry (and not the good kind of DRY ) if you need to go outside the Rails constraints.

Rails is, as I like to call it in a loving way, paint by numbers programming. If you stick 100% to the conventions (i.e. stay within the lines and use the colors you're told to use) you can make decent applications quickly and easily. If and when you have to deviate though, Rails can go from your best friend to your worst enemy.

2) When All You Have Is a Hammer...

Rails does simplistic CRUD applications very well. The problem comes when your app has to do more than just read/write from a database. Now, for the record the last Rails version I used was 2.3.4 so things may have changed since then, but I ran into major issues when business requirements changed so the application had to have a small workflow system built into it, and integrate with a legacy PHP application. The Rails convention of "one form, one model" works fine for trivial apps and data entry applications, but not so much when you need to do processing logic, or have workflows, or anything that isn't the typical "User enters data into a few text fields, hits Submit" type of thing. It can be done, but it's by no means "easy", or rather it wasn't when I last used Rails.

Also, Rails does not like to play well with other applications that aren't using it's preferred methods of data access; if you have to interface with an application that doesn't have a "Web 2.0" style API, you have to work around Rails instead of with it; again I speak from experience here as this is what happened to me.

3) It's New

Finally, Rails is still the "new kid on the block" in many areas. This doesn't matter for personal use or "I think it's cool and want to learn it" type of scenarios, but speaking as someone who would prefer to use Rails at my day job, if you aren't in a location where Rails is widespread, it can be very difficult to find fulltime work as a Rails developer. It's still largely the domain of "hip, new startups" and not a major player in most metropolitan areas. Your mileage may vary in this regard, but I know my area (Tampa) Rails is essentially nonexistent.

4) Fire and Motion

Rails is ever-changing. This is both a good and a bad thing; it's good because the community evolves and embraces new concepts. It's bad because the community evolves and embraces new concepts. It can be very overwhelming for a Rails newbie because typically when you run into an issue, and look around, you'll see either people recommending such-and-such gem to fix it, or saying that way is bad anyways and you shouldn't use it, here's a better way... and you end up having a laundry list of additional tools to learn along with Rails to keep up with the Rails cognoscenti. Things like Git , BDD/RSpec , Cucumber , Haml/Sass , and a cornucopia of other things all float around and get pushed as the "right way to do things" in Rails-land, and speaking from experience you may end up being swamped trying to learn a dozen or more technologies in addition to Rails, because using the standard Rails toolkit feels "wrong".

This is now compounded even more by Rails 3.1 making Sass and CoffeeScript of all things the default, so a total Rails newbie not only has to learn Ruby and Rails but Sass (arguably simple if you know CSS) and CoffeeScript (not crazy difficult but certainly different enough from raw JavaScript) at a bare minimum to get started, plus it can be assumed Git. Even without factoring in RSpec and friends, and the dozen or more gems that you'll typically end up with, that's 4 different things you have to learn before you can seriously begin to write Rails applications. Compare this to a language like C#, or Java, or even PHP where your HTML/CSS/JavaScript/SQL knowledge isn't going to change and you just have to learn the language itself and perhaps the framework nuances.