I am not familiar with DMR and analog used on the same repeater. I know Yaesu Fusion has that capability and it is a nightmare. I have a bunch of Yaesu Fusion repeaters in my state, quite a few within range of me where they work better than some analog. I will not even program them in any radio because analog never gets used on them. They also happen to be linked together digitally, so when someone on another repeater wants to run digital decides to jump on and start talking to someone, they will walk right over me. I could just upgrade but I barely use the radio as it is, so a $400-$500 price tag for something I barely use is a bit much to choke on. I would hope a DMR/analog repeater doesn't behave the same way?
When it comes to the bubble pack radios, digital would impact them. Tone squelching them wouldn't matter. If a digital signal comes across, it is still occupying that frequency causing the signals between the bubble pack radios to be diminished to the point where they wont be able to use them, just like I could take an analog radio and jam a digital signal if I am closer to their radio than the transmitting station. I am not saying this would happen all over the place, but with no coordination or the lack of studying who would get negatively impacted, someone out there would be out on their communications.
The other thing with digital is that it doesn't work as well as analog. I have been in so many situations where my signal either didn't get through, or it was so garbled no one could understand me. On analog, the other person could have at least heard me through the static. With digital, either you are there or you are not, there is no middle ground. Digital should be left to Ham radio, OR petition the FCC to create another GMRS like band. There are a lot of abandoned frequencies over the country ever since they rebanded things and many public safety agencies went up into the 700/800 MHz band. Personally, I would love the FCC to make those left behind frequencies available to those who want to play with them.