I had the same problems, sorted them out then they came back. For me both are easily explained.
First Ill try and answer Fuppes issue. Fuppes can be very hit or miss as to whether it builds the database correctly. If you have thousands of mp3’s to scan I would suggest giving up straight away (probably not what you want to hear).
This used to work fine on my Freenas but the Drobo seems to get about 2000 tracks in then gives up and crashes hence I now use Firefly for my music and just use Drobo for other media which I don’t store so much of e.g. photos.
With regards to Firefly not working…well for me it was a case of being a little patient. What i got was it appeared to install correctly but I couldn’t access the page at http://192.168.2.100:3689/
What I did may seem simple but give it a go. Download the mt-daapd.tgz file and upload it to your “DroboApps” folder.
At this point restart your drobo. Don’t bother using the restart from the drobo admin page as this doesn’t always appear to work, instead use the drobo dashboard to put the drobo into standby. When ready unplug the drobo for 10 seconds then switch the power back on.
Once the drobo has rebooted load itunes then wait for “Drobo” to appear under “Shared” on the left. Now wait…seriously you’d think the admin page for http://192.168.2.100:3689/ would be active now but it isn’t and this is were i spent about an hour restarting my drobo, deleting the software etc. and wasted time. Give it 5 minutes then visit http://192.168.2.100:3689/ and you should be greeted with the mt-daapd screen.
By the way the default Firefly password and username is mt-daapd