Your biggest challenge in owning more than one truck that you don't drive yourself is finding quality drivers who are reliable, honest and will take care of your equipment. If you can find good drivers you can make money with more than a single truck. However, we don't really know what is going to happen with this economy. I would not go much into debt until the dust settles. I would suggest that you start with one truck that you drive yourself and if you see that there is sufficient business to add trucks, then you can start spending money on additional trucks. If I were planning on buying dumps, I would go with trucks that are already set up for dumps. Using an otr truck for a dump is not a good idea. Dumps often have heavier frame rails or double frames whereas the otr trucks are not as heavy duty or designed for off road work. A dump can haul as much weight on just the tractor as an otr truck will haul with a tractor and trailer.
Some things to consider when thinking of buying more than a single truck. Hiring a driver means that you will have to pay a salary and likely some benefits out of any profits. There are some drivers who will abuse your equipment and steal or sell fuel, etc., Insurance and other expenses will increase significantly with each additional truck. My dad owned dumps and he seemed to always have problems with drivers. My niece and her husband also owned dumps. Like you, he did all the maintenance himself. Drivers can be hard on equipment. I would take it slow and easy. Like I suggested previously, I would start with a single truck that you drive yourself and see how it goes.
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