At least you have a truck :) I am renting out a van 3-4 times a month to do deliveries of stairs or long railings.
I have the exact same dilemma. I know for a fact that newer vehicles will have less headache at first and less down time, but at the same time, me personally, I don't have the capital yet to get one and don't want to and on the other hand - really want to get at least something!
Stress with my van rental company is getting to me from time to time. One day they have the van, the other they don't. You have to call them and make sure they will have it and so on. Also i need to get the tools from my shop in to the van and back to the shop when i am done... which is also - time and time is money.
I understand your pain. When we used rentals, there was almost always some drama associated with our reservation. You may want to consider looking into purchasing a used U-Haul box truck. They are extremely inexpensive compared to some alternatives and have complete vehicle maintenance history etc. In my area, 15 foot box trucks from U-Haul run anywhere from 7k-12k depending on how beat up the truck is.
