As for the tools, I'm surprised Hero Lab wasn't used. Pathfinder is an incredibly complex game and the folks at Lone Wolf have done an amazing job at keeping up with the new releases. The only drawback to it is that it's rather pricey if you get data from all the sourcebooks.
I hope there is Hero Lab support for 5E at some point in the future. I’ve only been a bit of a Hero Lab dabbler in the past. I’ve owned the program for several years, but didn’t really do too much with it when I was DMing 3.5E. They do have an encounter builder and other combat tools to help DM the game at the table. However, when I bought Hero Lab my game was already around 10th level and I just didn’t have the time or inclination to re-creating all the PC’s in Hero Lab and then learn how to use the software to handle real-time encounters. The manual method I had going worked well enough, so I just stuck with that.
After the end of the last campaign one of my players stepped up to the DM plate. So I got a chance to play in a 3.5E game for the first time in about a decade. I decided to create my character (a Gnome Wizard) using Hero Lab. There are still a few bits to the software that I need to wrap my head around, but it was definitely a lot quicker creating a character using Hero Lab than by hand.
Levelling up is quicker too. I only need to worry about things like choosing which class to go up in, roll hit points, allocate skill points, choose 2 free spells, choose a feat (if required) and increase an attribute (if level 4, 8, etc.). Everything else is updated automatically, so the whole process takes a couple of minutes.
After that I generate a PDF of the new character sheet, as well as my updated list of spells, print them off and I’m done.
The 3.5E Hero Lab licence only covers the rules from the OGL, so core rules only. However, users have created data sets for most of the WotC splatbooks. So, when my Wizard learned a few spells from the Spell Compendium I was able to add them just as easily as adding in a spell from the PHB.
I was disappointed to discover that no one had created a data set for the Complete Book of Eldritch Might (Malhavoc Press), so when I wanted to add in some spells from there I had to create them in myself. There is an editor for that, which made the process manageable. It took me a couple of hours to enter in all the spells I wanted, but most of that was typing up the spell info (spell school, range, saves, spell descriptions, etc.) I’ve since also created a couple of custom magic items without too much trouble.
My problem now is that I’ve spent several hours learning how to use Hero Lab, but this will likely be the last 3.5E campaign for my group before we switch to 5E. Now that I’ve seen how much quicker things can be with digital tools, I don’t really want to go back to doing things manually.
So I really hope that we see a 5E version of Hero Lab sooner rather than later.