When my previous employer transitioned to MotoTrbo XPR6550 handhelds and XPR4550 mobiles, I was tasked with attacking the system. They wanted to know if it could be listened into. I used another XPR6550 and then a USB dongle, even made the local Motorola salesman a little scared. Especialy when I told him how much the dongle and a better antenna cost. (Maybe $20 or so.)
This company was only licensed for analog mode, but digital was tested, and they also didn't want to spend money on encryption. Considering who it was, I think they should have spent the money on better radios, encryption, and digital licensing.
I'm in another line of work these days, and working more on VoIP phone systems now, and radios as a fall back. My previous employer is still using analog only and encrypted XPR radios.
I am amazed at how much is still analog and in the clear. I have an older Uniden scanner on my desk and am hearing local UHF comms from the state patrol. Drivers license checks, sometimes local vendors asking for price checks on items. Analog is not dead.