My lack of residential experience is showing through [Linked Image]

I'm moving and upgrading the service - sooner than I would like because the roof needs to be redone.

The stucco on my place has seen better days.
I fear that trying to surface-mount the base and mast will finish it off.

That leaves me with smashing the stucco off the immediate area, and mounting the base & mast directly to the sheathing. Patching the stucco afterwards I don't mind, but this arrangement will leave the area behind the base and mast unfinished. Is this a problem?

Who's got some good ideas? Space it out somehow?