When I reflect on the ease of use question, I realize most of my frustrations with the Clojure REPL have actually been with trying to use it within an editor (Vim, Emacs, and Atom so far). And particularly with getting a ClojureScript REPL through those tools. That's not something I try to do with Pry, being content to use it from the terminal, so maybe not a totally fair comparison.
The app environment thing is mostly about having to switch between a lot of namespaces and/or to make sure they're all loaded upon starting the REPL. With Rails+Pry, you can work with any class in your app immediately. It also lets you put breakpoints in your code, where executing the code in a running process throws you into a REPL at that point, with all the local context up to that point of execution. Also, if you make code changes, you simply type "reload!" in the REPL and everything's up to date. I have a bookmark to read Stuart Sierra's post about his workflow to try to get a grip on how to come close to something like that in Clojure.
Have you tried using Cider under Emacs? Or Cursive? Both of those have debuggers that allow you to add a breakpoint in your code and then evaluate arbitrary expressions. They also allow you to step through each form and see the return value.
There are also a few projects for adding in debug REPLs, but those seem to have fallen by the wayside lately, perhaps supplanted by debuggers.
You might also want to talk a look at Duct (https://github.com/weavejester/duct), which is my ongoing and still early attempt at solving some of the framework problems with Clojure. If you create a template via Duct, like so:
lein new duct foobar +site +cljs
Then you some of the things you're asking for. The namespaces of your application are loaded when you start `lein repl`. You get a `(reset)` function that reloads your code, restarts your application and pushes those changes dynamically to the browser. You also get a ClojureScript REPL that hooks into the browser.
There are also generators, migrations, database support etc., but currently all inferior to Rails. I'm probably going to be working on the generators next, as they need attention.
The app environment thing is mostly about having to switch between a lot of namespaces and/or to make sure they're all loaded upon starting the REPL. With Rails+Pry, you can work with any class in your app immediately. It also lets you put breakpoints in your code, where executing the code in a running process throws you into a REPL at that point, with all the local context up to that point of execution. Also, if you make code changes, you simply type "reload!" in the REPL and everything's up to date. I have a bookmark to read Stuart Sierra's post about his workflow to try to get a grip on how to come close to something like that in Clojure.
And it can do a lot more great stuff, too: https://www.youtube.com/watch?v=4hfMUP5iTq8
Oh and by the way -- thanks for all of your OSS work in the Clojure world! Especially taking the extra step of providing good docs.