PDFs as separate files?
 

Is it possible to save to pdf / print the entire portfolio, but have each character's PDF printed as its own file rather than a single large PDF?

No. You should be able to break up the original into smaller files with a separate program.

EDIT: You can print each character separately as its own PDF, or the whole portfolio as one PDF. There's no single option to print the whole portfolio to PDF and have it separate the individual heroes into their own PDF.

I thought there was an option for just one character to be printed, whether to paper or PDF.
And something to enable/check for the entire portfolio to be printed.

If you save to PDF/print a character at a time, several steps instead of one, you can have each character as it's own PDF file.
I do that for the players who play remotely in our game.

My Hero Lab (classic, because we use Community Pack and Sphere packages heavily) is the official version.
Players get a new sheet (or PDF) each week, with any update to their character.
Two have liked HL enough to start buying pieces of it, but most finding 600+ to daunting to buy it and don't want a partial access... so just have me build a character with them, they make the choices and I enter to make sure the build is legitimate.

Yeah, I've been printing them individually, I was just hoping to be able to click a couple times and get all my players' sheets at once rather than select, print/export, save, select location, wait for it to finish, etc. :)

Thanks all!

I don't know how comfortable you are with scripting, but there are command line tools that can split a PDF into separate pages. For example, pdftk and qpdf are two (both of which I use). I've used a scheme that prints the entire portfolio, then run a script that extracts the first 4 pages to "ugliwarto.PDF", the next two pages to "barton.PDF", and so on. It becomes just a couple clicks (one to generate the PDF and another to run the script).

Because the script always uses the same filenames and always uses the same number of pages, it's not a very sophisticated script! (Sometimes I have to update it; for example, when a spellcaster gains a level and their list of spells spans another page.)

HTH. YMMV.

Interesting. I do a decent bit of powershell scripting for work, so while I'm not what I'd consider a coder that might be within my comfort zone. Thanks, I'll check it out.