If a new drop is required do utilities charge for this or is it one of
those gratis things they do in hopes that you'll buy more power?

If the panel ought to be replaced is that a nightmare of replacing each
conduit from the panel to its first junction box or do they just try to do
some bending to align with the new box's knockouts? Pull the wires back
temporarily and shove them back on into the new box? I guess every pipe
could be cut short and a bit of flex put in or a conduit joiner to a new
short piece with the required bends. Just wondering if there is a standard
way they do these things or if each case is so different there is no
telling. Even if one had a new panel the exact size of the old with a
close match on knockout availabilities it would still seem like a big job
to get it in and pipes into conduit connectors but maybe there are special
ones to ease this. Seems like this would come up quite a bit.