Need advice on starting business

Hey guys. I am new here obviously and I wanted to start my own thread to get some advice. I have read through the forum for a couple weeks now to try and get a base knowledge of the industry and what is needed to get in it. It has been a wealth of knowledge and it seems like there are so many knowledgable members here on the forum.
I have seen so many people that buy equipment and then come here to find out how to go from there and how to make money. I dont want to be one of those people and I would much rather have a plan put in place and go from there.
A little back story on myself. I am a finance mgr in the car business and I work for a Dodge dealer. We have a pretty big commercial dept and I have talked to a lot of guys who have bought trucks to start a hot shot business. I would like to start with a truck on the road myself. I have a good friend of mine who has his cdl and is retired so he doesnt have to be busy all the time while we are starting out. He has his retirement income and would do this with me just to make some extra money on the side.
Here is what I was thinking. I would buy the truck, trailer, and all necessary equipment and all expenses associated with the truck. Get all the paperwork and license taken care of. I would book all the loads since I have a bunch of free time at work and am always on a computer. He would run the loads for me and we would split the profits a third to him, a third to me, and a third to the truck.
At the beginning, I really am not worried about making a profit as long as he makes a little money and the expenses and truck and trailer payment get made. This will give me some time to learn the ropes and get better with the loads.
Some questions I have are:
Since I wont be driving to truck, do I have to have my CDL as well.
I have read the steps of getting legal on the road but I would like to have them here just to make sure I have everything I need.
I plan on getting a 3500 cabin chasis so what is the best trailer to get with that to be the most versatile and be able to do the most loads.
I have tried searching the load boards to see what kind of loads are out there in my area but they want me to sign up for a service and give my numbers which obviously I dont have yet so what is the best way to do that type of homework before I actually start getting my numbers and authority.

I would appreciate any advice and constructive criticism. This is a way to help him make a little extra money and hopefully an investment for me as I get better at booking loads. Thanks guys

 

I am keeping my day job. I will be doing this at my day job. I have a lot of extra time to try and put together loads. He is ok with not making a ton of money because this will.get him out of the house and supplement his income.

 

Also, any advice on the trailer that would make me be able to be the most versatile would be greatly appreciated. Again, i am thinking of going with a 3500 cabin chasis as the truck

 

I know you where joking with that post but those trucks are very cool. Lol