It would be a terrible idea to buy multiple contracts all at once, probably not very practical anyway with how long the process takes with FedEx. Even shadowing your friend, you’ll learn a lot with your first one and have a much better idea what to look for in a second. You don’t want to compound any costly mistakes by making them over 3-4 contracts instead of 1. After you get one going you might even be able to pick up distressed areas for free and use your capital for only equipment instead of buying another contract.
To another of your questions further down, I think FedEx is currently weeding out contractors that are less adaptable to improve their base for the transition to One FedEx. They’ll have to increase compensation some to maintain service when they make that switch. It won’t be a ton of money but they’ll need a more stable contractor base going forward. A lot of people got in or expanded during Covid and don’t know what they’re doing. Many overpaid for contracts and are going bankrupt because of the debt they’re carrying.