Thanks everyone for your input and advice.
The roots don't feel loose to me. But I'm going to look into whether there are any burrowing critters around here.
Big apple rose guy: I'm not sure what you mean about brick flooring, but there Isnt anything that hasn't been there for the past 10 years. The plant has an ample bed of soil . However I do wonder if the issue maybe to do with watering. The past month has been dry and I probably should've watered more. Trying to make up for it now.
I'm also interested in the black spot hypothesis. Does anyone think I should do some kind of chemical application?
This is an old rosebush. I have quite a few other varieties of roses and they were my dad's, so I would like to keep them going. They are also old and probably not disease resistant. They're not in the best of health but they are hanging in there for the most part. I applied Rosetone last year, and some are doing a lot better. However two bushes died this past year.
I am posting a few more photos of the entire Bush, and a close-up of the base of the plant.
Thanks again everyone. It's nice to confer with fellow gardeners.