Would I need to purchase a second Roon license to have it work in a second home or at my office?
At the same time no. If run independently yes. You can only authorise one at a time.
You can load the Roon core software onto as many computer devices as you want. However, with only one license, you can only use one at a time. The problem that arises is there is no good way to keep two or more cores in sync other than doing a backup of one and then restore that backup to the other using a USB drive or some such device.
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I have a Roon Core on an iMac and MacBook and it is annoying having to deauthorize one or the other. If Audirvana can do it why not Roon, after all the licence for one year is a lot more then 1 licence for Audirvana.
One idea would be to have the license key on a USB stick, then you could just move the stick between cores to authorize. Periodic checking with Roon’s servers could still occur, but more in the background.
It’s a kludge no matter how you do it. I would suggest avoiding multiple licenses until Roon figures out how to sync cores.
I do not need to sync cores necessarily. On my iMac i use Roon to playback my HiRes files as that is where my DAC and Hi Fi system is, and although I have my ripped CD’s on the iMac I use the CD player in that room. My MacBook has the ripped CD files and purchased iTunes AAC and MP3 files, and as I have a Qobuz subscription I can access my purchased files within the core or use Audirvana for both Qobuz and HighRes audio purchases. May sound convoluted but works for me.