250 vs 350

I’m looking at probably a 2017, 18, 19 ford diesel. I have a concrete and landscaping company and will be hauling a medium sized skid steer in a dump trailer. I’ve been finding some nice 250’s for several thousand dollars less than the 350’s. My question is, do I really need the F-350 if I find a much better deal on a 250? Will I be kicking myself in the ass down the road if don’t go with the 350? I’ll probably drive this truck for a minimum of 10 years so I don’t want to regret not getting something capable of pulling what I need it to.