I would use the service! I think it is a great idea and $250 is a fair price.
Things I would like to see is UP TO DATE and ACCURATE schedule for pickup and drop offs with load/room info.
For example, I have no issue with a game being picked up and sitting on a trailer for a few weeks till you make it up my direction, but I would like to be able ot sign in to see where you are and when you plan to come by.
I can also see using this data to look for pins. For example if I see that you will be in STL area next weekend and have room for 4 then I may look to see what is available from sources in that area.
A big part of white glove service is good communication and knowledge of where my game is enroute and where you are for possible pickups.