UPS will give you $100 per box lost, period. The claims department will do all they can to pay you the lowest amount possible.
So declare the value, photocopy receipts, take pictures of what you are mailing (be a paranoid attorney), because this attorney is out over $500 after shipping 3 bulk shipments of at least 10 boxes each, and UPS delivers 3 bulk shipments (where the recipient signs 1x for several boxes) and then there are 2 boxes missing from 2 shipments. UPS said 1 had arrived because it had been signed for (once as part of a bulk shipment) and another was "lost" although the other 9 boxes were shipped together and arrived together. If you have to use UPS (USPS is cheaper by A LOT), then fill out every box in the forms, declare values, itemize what you ship and prepare to battle get what you paid for.
What a terrible experience. Very disappointing.
Monetary Loss: $550.