Yes on both questions. There are several step by step procedures that have been posted. You might consider (along with your tech) to reach out to François as he is very knowledgeable in these areas including current experience with Mac's.
As well, you can go to each of your sample set producer's web sites and download the appropriate updated sample sets they offer (free) that are compatible with Hauptwerk versions 5 and version 6. Obviously, depending on the number of organs you have, this will require some drive space. Here, again, François, can give you good information as to how best to go about doing that.
The other thing you can do (ahead) is to establish an iLok account hy:
1. Go to the iLok website.
https://www.ilok.com/#!license-manager 2. You will see the iLok License Manager - Click on top line -
Create Free Account3. Choose the right License Service Installer, depending on your operating system: Mac OS, Windows 32-bit or Windows 64-bit, or click "Legacy Installers" if you have older versions of Windows or Mac OS.
Rgds,
Ed