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I am the owner of lvh.me. And I'm glad to hear it's helpful. In truth, it's just a fancy DNS trick. lhv.me and all of it's sub-domains just point back to your computer (127.0.0.1). That means running ssl is as simple (or difficult) as running ssl on your computer.
I'm not sure how comfortable you are with the command line, but here's my how I setup my development environment. (rvm, passenger, nginx w/ SSL, etc).
# Install rvm (no sudo!)
# ------------------------------------------------------
bash < <( curl http://rvm.beginrescueend.com/releases/rvm-install-head )
source ~/.rvm/scripts/rvm
rvm install ree-1.8.7-2010.02