flatbed vs. dry van

I'm planning on starting into O/O trucking as an experienced business owner, but as a new OTR driver, while maintaining my profitable current, unrelated business that requires little of my time.

I've been lurking and researching, but am unsure whether to buy a 53' van or a 48' flatbed with a rolling tarp system. I can't see my old ### getting on top and tarping as I'm not so comfortable with heights above, say 10'. On the other hand, if I have a conestoga type set up, that would eliminate tarping altogether, right?

so, I've been thinking that I could start out with, say a $10,000 used air ride dry van, which is decidedly less expensive than a comparable 48' x 102" skateboard, especially equipped with a $14k tarp system.

I will likely pay cash for a tractor with about 500k on it. Not likely a Ken or Pete, but a Freight liner or possibly an international. I'm thinking a DD15 or possibly a DD13 with a 13 speed, that can be rebuilt when necessary by a decent small time mechanic (not me), not an uber expensive major fleet repair facility.
I also get that maybe a 3.36 up to about a 3.55 would be likely a good rear end ratio for overall pulling and economy blend. Does that sound about right?

I was going to get my own authority right off the bat, since I've had a DOT number since 2002 (like maybe that would help my insurance rate), but since have come to the conclusion to sign on to a Land Star or small carrier paying 80%, as I have learned the insurance rates are substantially less for o/o leasing on, rather than own authority. As for self dispatching, I've been in business for 30 years and can negotiate as well as anybody I've met. DAT seems to simplify finding loads and comparing moving averages and other criteria.
Gotta lov that!

If any of you guys or industrious gals have thoughts, particularly on flat bed vs. dry van, the ups and downs (pun intended) and whether a different type of tractor is needed for one over the other, please speak up. I've got money, but not so much that I would spend say 70k, if I can spend 50k and still get the job done.
What year of truck for around $32k - $42k give the best bang for the buck at today's used rates, given someone who shops and has cash in hand?

 

I appreciate your answer. Flat bed isn't for me, in that case. I am 6', but very small in terms of a business man's pocket book. However, I don't think having money disqualifies me from driving. Sometimes its nice to be able to make a decision to do something because I have the money to allow me the freedom to do it, and not have to do it. that may not make sense to most people, but I'm as much adventure seeker as I am up for a new challenge. Do you know anybody that wants to trade a rig for my Cataline C30' diesel powered sailboat?

 

Ok. I see. So, even placing your truck where the best freight is based on posted loads, you're saying you can't have 9 or $10,000 weeks (gross of course) with a dry van? I understand that not $3.00 per mile loads aren't going to be common for long runs. The guys who I follow, (just a small hand full) average around $2.30 when they show their monthly breakdown to the truck. Is that not your experience? Naturally, markets change, sometimes from one week to the next.

What do you usually haul? Knowing what you know now, if you were able to haul exactly what you wanted to (maybe you can) with your extensive history as a trucker, what would you haul and what truck would you buy for a first time, used truck (say under 45k). I am actually thinking about buying an older, say 2005 truck for 10-15k and putting another 12k or so into it, but I'm not sure the best approach to get a truck that will make me the most money and cost me the least headaches. it's a balance, for sure.