Your license will remain active.
You cannot upgrade directly to the latest versions. Due to a file structure change, you need to first go to version 9.0(4) or 9.1(2). Once you do that, you can continue on to the latest version in the release train you're targeting (9.1/2/3(x)). Reference.
Other than that, it's a pretty painless upgrade. I've done it many times without issue. Be sure to upgrade your ASDM while you're at it (if you haven't already).