MG84, I apologize for getting so far off topic. The questions you have posed are addressed by every small contractor when starting out. I rented all my equipment in the first years of business, and had the dealership deliver anything bigger than a skid steer. My thought at the time was that I could always have exactly the right equipment for the job, be more efficient, and look more professional showing up with newer equipment. If I had an issue with any of the equipment the dealership was there immediately to address it. That was in 2008 though, equipment availabilty was not an issue and the dealership would subsidize the hauling somewhat.
Since then we have moved to a point where we only rent various equipment two or three times a year, and typically for a relatively short duration. The biggest reason for the change is that availability became a real issue, especially in the last three years. Also, we were putting 500 or more hours per year on our primary equipment and the cost per hour of ownership became lower than the rental rate. Add in the convenience of having your machine right there ready to go has a lot of value, just hard to put a number to it.
In regard to hauling, trucks are just a necessary evil, especially for a contractor getting started. That said, for the size of equipment that you have I also believe that a dump truck with tag trailer is probably the best way to go. It will free up scheduling, allow you to go get your own aggregate and have it available when you need it rather than altering the job schedule around material delivery, and allow you to move to the next job at your convenience. That said, if you have a good relationship with another contractor or aggregate company that will haul your equipment for you, it probably makes more sense to invest in the equipment first. It will become clear when you need to invest in a truck.
I wound up buying our transport before equipment. The reason was that it became difficult to have our rented equipment hauled from one jobsite to another. We typically use nothing smaller than a 200 size excavator, paying rent on one for a day or two and the loss of revenue while awaiting transport didn't settle well with me.
A lot will have to do with what you have available in your area as far as companies to transport your equipment.