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Having a CDL won't increase your insurance, but commercial and heavy vehicles are usually more expensive to insure than passenger cars. Trailer weight ratings are based on the axle capacity. IMO get a dump trailer with 7K lb axles but only 2' sides. That way you'll never be able to put enough...

The worst part is overloading your tow vehicle. What kind of tow vehicle will you be using and do you have a CDL license? If your trailer is over 10K and the combination of truck and trailer is over 26K then you need to have a Class A CDL. DOT cops love pulling over guys driving an F350 pulling...