Small Time Trucking Qestions and advise needed....

Im Glen, Fairly new to the trucking industry as a driver that is however I grew up around it.
What I want to do is start up my own Side Business so to speak. But I want to get all my Ducks in a Row
before I jump into something.

What I am looking to do is start out with what I have and Grow from there, I am tired of working for people and want to run my own business.
I have the following
Chevy 1/2ton Pickup
6x12 Enclosed trailer
6x12 Open Trailer
Access to, a Single Car Trailer and multiple variations is size open trailers that I borrow from friends all the time.

I would like to start out doing weekend Runs, Also have a friend who is 30 years in the business and willing to run during the week for me.
Would primarily be doing Local hauling 300-500mile radius from where I live in North Jersey.
My goal is to Start small and easy and grow enough over time That I can get out of were I currently work and
make a full time career of something I love to do. I currently get calls from some friends in the Business
to do loads for them from time to time on weekends when I am off (I have my class A)

What I want to know...

Has anyone tried anything like this and how well did it work out for you?

What are some other insurance companys for comercial vehicals in NJ other then Progressive?

Will I need Business Insurance on top of my Vehical and Cargo Insurance?

I know I need a DOT number but will I also need a MC number?

Do I need Apportioned plates on a pickup to run out of state?

Any other Input anyone Wants to give me, Im the rookie here, I know that and I just want honest advise.
Im sure Ill have more Questions to follow but this is a good start for now, any and all help would be appreciated.
Thank you

 

Just realized I probly Posted this in the Wrong category, Sorry.......If It can be moved or deleted Please do that and Ill re-post if I have too.

 

Thats pretty much what I figured as far as the truck goes, Ive been looking
Around for a dually, but If I am going to spend the money on a truck I am being a little picky
as to exactly what I want and thats proven to be hard to find around here plus
everyone thinks what they have even if its garbage is gold and worth way more then
it really is welcome to jersey lol but for now at least I can get some advise and get a start
in the right direction...

 

Yeah well most pick on the new guy so thats ok.


Thank you

 

Any imput on the fact of doing this as a weekend job to start? Trying to stay with my regular job for the time being and build up before making a complete transfer.
I do get a lot of 3 day weekends were I am.