Jaybird, I love your enthusiasm, but your going to wear out your vehicle/equipment & not make enough money to barely do maintenance & buy gas, let alone make enough $ to replace your current equipment. And what is your time worth? $250 is crazy cheap! I live in Northern Michigan(310 miles N of Ohio) I drive a lot for pins. For $250+- I will gladly use your service. Just be sure to figure in All of your expenses with your shipping Co. it's a lot more than you think. Maintenance alone can eat you alive.
I should mention that I own my own shipping/delivery company that subcontracts to FedEx Ground. Here's a picture of a third of my fleet.

IMG_20160702_080405184_(resized).jpg

That would be the ideal situation for sure, & if your going to cover your cost it's a must.

Jaybird,
If you don't mind me asking. What year make & model is the vehicle your going to use for towing? And is it a gas or a diesel?

It really should be a diesel when ever you are towing or pushing(plowing snow). You burn less than half of the fuel of a gas engine. It also comes with an extra heavy duty transmission(Alisson) with coolers.

Don't get me wrong, I love this idea! I'm just trying to help Jaybird from experience over the past 7 years of owning my tucking business. Maintenance really is a wild card. One month it's low, the next it is high. You have to make enough money hauling these pins to not only set money aside for: fuel, brakes, rotors, & tires. But also the really expensive ones, like transmissions, rear ends, an engine & to replace his current vehicle some day.

Great point! How in God's name could I forget this cost! Lol
Liability insurance. Not just for the pins, but for the homes you go into & will no doubt at some point do damage to.