The only water shutoff valve for my house is located in a recessed box
at the front curb, some 50 ft away. Using it requires a special
long-handled "tool" which is kept in the garage 80 ft in the opposite
direction. Adding to potential for confusion, the valve itself is very
unclearly marked as to on/off, plus there's another valve for the entire
street just a few feet away, which this tool also operates. With +100lbs
water pressure this makes me very nervous about how much water could
potentially spill should something disasterous happen.

It looks like the pipe runs underground up to the footings, either under
or through the footings, and vertically up on the inside of the
foundation in the crawlspace. Can a pumber add a shutoff at the house,
by drilling through the foundation? Are permits usually required for
this kind of work?