If you can find stuff used and cheap, I don't see what you have to lose by starting your own business on the side.
I'd suggest a truck with a diesel engine if you can swing it. And take a look at Mahindra tractors.
They're good machines and they're much less $$$ than Kubota or John Deere.
I'm looking at getting a used, small dump truck...like an F350 Dually...but, I want to buy whatever tractor I get new....with a good warranty on it....there's a lawn and garden place 2 miles from me that just started selling Mahindra tractors....my main worry there is if they were to quit selling them...many more Kubota dealers around here......
I looked at some Branson tractors(made in South Korea like my Kia)...same thing...service and parts availability long term?......
We've got an F350 super duty diesel box truck at the day job with around 430,000 miles on it. They use it several times a week. I schedule the maintenance and repairs on it. Service is expensive but the truck just keeps on running.