A little late to join the party here, but thought I'd chime in. I started a business last fall and am probably going to disagree with everything you all say!
I was considering setting up a business using dump trailers, figuring it would be a cheap "in". I could use my pickup to move them, so it would only be a minimal investment in a few trailers. I got turned on to hook-lifts and started digging. My goal was to fill the void that the bigger companies have left by not having smaller containers. I also wanted to stay under CDL: less red tape, no license, easier to maneuver in small places, etc. I walked into this with zero experience in the waste industry, and my only experience driving was in my dad's box truck.
I settled on a 2007 Hino 268a...Pre-emissions and under CDL. It has proven to be a hell of a truck; I bought it from Brion Maguire from Trucks and Parts of Tampa (at his PA location). Then, I had a local company (Donovan....two thumbs up to them!) install a Pioneer hook (18,500 #) and a Pioneer tarper. The hook will serve 36" or 54" hook heights.
I bought dumpsters from International Container...10 and 15 yd tub style with a 54" hook height. One of the big advantages is that the hook is higher and more visible, especially when it snows.
I can't say enough good about the set up we have. We have a capacity of about 5 tons, which *usually* more than enough. We're filling a void that the "big boys" don't want. The cans are perfect for home cleanouts, smaller residential construction, and roofing. We've already purchased our second round of containers. Someone here mentioned the hook having an advantage because of the wide approach angle....absolutely correct. I can set the dumpster almost on the ground and shoe horn it in about anywhere. Then, to pick up...I can back up at a 45 degree angle and get it right on.
Could the Hook move a little quicker? Yup. Would I like a bigger truck? Yup, someday. But, we found a void and we're filling it. We're right where we want to be after just getting in the business 8 months ago.
I will say, I wouldn't go with any smaller of a truck. You just won't have enough capacity. I don't know that you'll find that much of an advantage in going to a 33,000# truck...plus you'll need a CDL!!! Is it THAT big of a deal? No. But I've found that the set up we have is giving us the experience and reputation that we want. When we grow, we'll definitely move into the bigger truck/cans...but for now we're doing extremely well. Our customers know what we offer, and if a job is too big we tell them so. They appreciate the honesty, as opposed to just jumping ship. We also find that people don't want to use the "big boys"...rather, they WANT to deal locally.
Did I have to invest more than I wanted? YUP. But, when I made that switch it's when the concept turned from a hobby to a business...and in doing so we brought it to a whole new level.
Do your research. Think it through. Ask questions. Take care of your customers. Take pride in what you do.
Do all of that, and you'll do well.