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Educate me on Commercial insurance (with private use)

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I have read as much as I can find and just wanted to get some personal experience information. I am contemplating a side business with a few trailers. It seems there is a demand and the possibilities have peeked my interest.
My truck and the trailers would have a GCWR over 26001 lbs but I do have a CDL. Being a "part time" job, I need to weigh whether the hassle of an LLC/Commercial insurance/DOT is worth the investment.
How many have only a commercial policy that use their truck for business and personal?
What will your commercial actually cover for personal use?
What are the best companies for adequate coverage and good rates?
My "commercial use" is short trips and local. Though the truck and trailer are rated over 26k, they would never be loaded to that amount. I understand that what they are capable of is all that matters, does commercial insurance take into account for weights in any manner?
Is yearly mileage a factor in commercial insurance?

Thanks for any help and insight. Any other information you would like to volunteer would be appreciated.

P.S. - Yes I have a CDL for my government job but I have never driven "commercially" for pay so I have never dealt with any aspect of commercial insurance.
 
Best advice I got was sign up as a member with OOIDA. Greg let me in on that.

They are pretty awesome and can help out with some of the forms and the sort.

Best $45 I spent in a long time. Lots of help on other stuff you might have questions on.

Forms like a BOC3 done in minutes, you need your membership number takes a work day won't have it over the weekend. Then your all set.
 
It's expensive. You may need a rider on the policy for a passenger even if you are married to the passenger. Declare the replacement value of your truck and equipment. Aim high! I made the mistake of "what I paid for it". I had just dropped an engine in it when it was totaled from running two elks over. They cut a check for the declared amount plus tax and plate fees. They also paid for the damage to the trailer. They re-insured it after I bought it back and rebuilt it.
 
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