I think that I might go with 5 5Hp drives like you suggested. That was my first thought. Have you done something like this?
First thoughts often end up being the best decisions.
I have not done something like this, but I have supported a handful of them. Its all fine and well until one of 6 contactors develops an intermittent problem and the technician is down half a day trying to locate the source of the problem. All he knows is the drive stopped and you have 5 OL contacts wired in series...
Just the basic premise that all relays fail, and the bigger they are the harder they flame out makes me dislike adding multiple contactors to a design.
If there is any advantage to keeping 4 of the motors operational while one has faulted or failed, then go with individual VFDs.
If the panel is laid out nicely, and some troubleshooting guidelines are followed, I think it could be just fine. One system I had to support was done that way, using one drive to any one of four different ballscrew motors that were only operated during product changeovers. It suffered from mismatched sized motors and a single OL setting so it would cook the little motor if there was a mechanical bind, until it's MPCB would trip which then had to be annunciated with another pair of wires and input point and reset manually....
Another system with fans, was great as far as function and reliability, but when any problem occurs, you lose all three fans for at least the first occurrence. So, in my opinion,. they all suffer from reduced flexibility and reliability. Single VFD multi-motor systems will increase troubleshooting time and errors, too.