Advice on starting a trucking business. Employee transition to contract deliveries

I am currently an employee for a produce company driving a company truck. My employer is a very busy small business owner and I have been delivering his product for in a 40' box truck for a couple of years. My employer is very good at what he does but is completely clueless concerning the trucking side of things. Over time I've ended handling all the licensing, logistics, and maintenance along with the driving. Handling all this work is often down right a pain in the butt because I have to report to my employer with everything I do. I often cannot get in contact with him for authorization in a timely fashion, and operations tend to be last minute and often bend the limitations of dot regulations. The vehicle maintenance is always a second priority to his produce business, and I often have to sort of bully him into keeping the truck in safe and legal condition.
In addition, there are some significant inefficiencies with the logistics that is leaving potential money on the table. Deliveries occur six days a week because the product is highly perishable. Tuesday, Thursday, and Saturday are local deliveries around 150 miles round trip but the customers can be slow so round trip can take between 5-8 hours. Monday, Wednesday, and Friday are longer trips around 620 miles, but are a 300 mile deadhead on the return. Long trips are 2 deliveries and I unload myself with a pallet jack, round trip is right around 14 hours. I have been trying to find him LTL freight to make him more money on the return trip, but 99% of the available brokerage is for FTL (I'm also the primary driver so there's no #### time to deal with brokered freight). His business is growing fast and he will soon need to trade in for a tractor trailer. I've realized that there might be an opportunity for me to buy a couple of trucks and trailers and contract the deliveries from him. I could have proper maintenance on the vehicles, hire a guy I trust to do some of the driving, and make my profit by capitalizing on dedicated or brokered return freight on the longer deliveries.
I'm a young guy, but I have 4 years experience driving over the road. This produce delivery job was my local driver transition. I have no experience as an owner operator, so I have a limited understanding as far as determining costs vs profitability. This forum has been invaluable to me during my transition years ago to get my CDL and go out on the road. I want to break down the potential finances and operation of my plan with the owner operators of this forum. I greatly appreciate your experienced feedback, criticisms, and links to your suggested educational research sources.

My plan is to buy two tractors, at least one with a sleeper, and two refrigerated trailers. My trusted driver or myself would leave the night before with the product on the long trips and deliver in the morning. After delivery, we would load with brokered freight and return to base. The next day, my employers local product would be delivered as usual, and the brokered freight would also be delivered if possible. Two drivers, two trucks, and 2 trailers; basically one truck is running full time, and the other is running half time or more if possible. I can guarantee with backups that my main delivery contract will be taken care of, and have the flexibility to deal with lying brokers or delayed delivery for brokered freight.

Breakdown for what I plan to charge my employer to contract loads. (I have limited experience with pricing so please advise)
M: $800
T: $250
W: $800
Th: $250
F: $800
S: $250
My current employer's business runs 52 weeks a year so the total contracted income would be $163,800. I'm guessing I could make another 60k to 80K organizing brokered freight on the return trips and the off days locally.

Do these figures sound reasonable to you experienced owner operators? I know I can't pull any brokered freight without buying a second tractor because my employer's deliveries are too time consuming. Do I go broke by buying a second tractor?

I don't want to be an employee forever. I fully appreciate the luxury of coming home every night and not having a care in the world, but my mental 10 year financial projections are getting louder and louder. Thanks in advance for your feedback.

Invicta

 

Ok good input. About a year ago when I was calling brokers to cover the long runs the cheapest quote I got was $1275 per load. My $800 estimate was a lowest case scenario combined with today's lowered fuel prices. Do you guys think this plan is workable with higher contracted prices, or is my 2 truck idea simply not feasible? One of the trucks would be doing lower mileage compared to the main one. I know how much it sucks to rent a truck for the day, so my theory was that taxes and insurance on a lower mileage truck could make some brokered freight possible logistically, while ensuring %100 dependability for my current produce loads.

I really have no clue how much I can make with brokered loads, or what is a reasonable rate for the dedicated route. My idea for two tractors is based on my experience with how unreliable most consignees are concerning appointment times and the general disrespect for drivers. I imagine some brokers will lie through their teeth to get their freight on your truck and leave you to deal with the delivery, so I want to make sure I have some cushion to make sure I can honor the dedicated produce deliveries.

If you experienced guy's were in my shoes how would you handle this delivery schedule, and what would your pricing be? Is this a one truck job? As the only driver I always feel screwed for time to handle regular deliveries along with extra deliveries and maintenance (on a Hino no less).