
GM Rednal |
Well, the big thing is that you'll need to have a way for both devices to access your data files - in Hero Lab, your portfolios are saved locally, so you will have to transfer between them somehow... maybe an automatic cloud backup of some kind?
On the bright side, Hero Lab gives you a free secondary license that you can activate on the iPad (albeit only for Pathfinder), so you only have to buy it once.

Tim Emrick |

It's been a while since I used the HeroLab iPad app (my tablet's too old to handle much of anything anymore) but if I recall correctly, the easiest way to transfer between the two was: 1. Get a secondary license for the tablet (which you'll need regardless) and 2. Email the portfolio file to yourself, and download that attachment on the other machine.

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Hero Lab has had Dropbox integration for awhile but they're removing it in the near future. No explanation, and no replacement has been announced. It seems to be based on the changes Dropbox has made to their API. Dropbox has promised to support the old API until at least September. But right now, Hero Lab isn't planning on supporting v2 of the Dropbox API. When v1 goes away, so does Dropbox support.
That means your primary method of getting portfolios to your iPad will be email, as suggested above, or using the Dropbox app and choosing to "Open in..." Hero Lab. Hero Lab is planning to enable Share and Open In menus in the next version of the iPad app, so you'll be able to save a portfolio back to Dropbox. This won't be as smooth as the current integration, but will be better than emailing.
GM Rednal is incorrect about requiring a license for both devices. The iPad app is free. It does not require a license to use as a character sheet in "Play Mode." Without a license, you cannot create new characters or perform character advancement and add new levels.
You'll only need to assign your secondary license to the iPad if you're going to level up or create new characters there (but then you'll need to mail that file back to your PC).