Looking to make a solid plan to go O/O in a few years

This comes up a lot in this board "how to get started" and I have read through most of them. There are many different situations out there so here is mine:
I'm at a junction point in my life where I think it's time to relocate to somewhere that is a little more friendly for someone to own and insure a trucking company.
I'm currently in South Florida, just about 15 minutes north of Miami. Housing prices and rent are high here, insurance is almost unobtainable and completely unaffordable without a massive amount of capital and the hauling rates are very low and hyper-competitive. I have been hauling heavy and oversize loads around FL and the southeastern US since 2013 as an employee of a reputable heavy haul outfit down here. I am a FL certified pilot car driver (my personal truck is a up fitted as a pilot car), i'm almost certified in rigging level 1 and do a lot of work with cranes.

I can run & build multi-axle modular trailers, stretch trailers, flatbed, RGN, Landoll,and any of the random things I've had to tow or haul over the last few years. I have mechanical knowledge, carry a lot of tools on my truck and have the knowledge to get myself out of most jams i've encountered with malfunctioning machinery. I also have a background in marketing and business development (that was my career path before I got a CDL.)

A little personal background on me: I am 30, no wife, no kids and no mortgage, I take care of myself, in decent shape and don't mind working long days and putting in the time. I've had a CDL for 6 years (5 of them doing oversize, specialized & heavy haul) and I still enjoy it just as much as the day I started.

I am looking to go O/O with a my own single truck operation in the equipment transport field sometime in the next few years at least. I am saving, saving, saving, but after doing my calculations, it is going to take me 7-10 years of living in a shoebox alone, not doing any life building (getting a home, getting married, having kids) to even have anything saved up to the tune of where I can get started and survive for longer than a few months here. I'd like to get out of this place and go anywhere at this point where I can afford to get a start into being an owner. Any thoughts or pointers on this would be much appreciated.

 

I'd like to own a Truck and combination of trailers to keep moving, most likely a RGN & step/flat or a landoll. I think starting at a good well maintained tandem tractor and stepdeck with a dovetail will cover quite a bit of the larger, not heavy oversize moves and not break the bank with equipment cost. Tri-axle heavy-spec trucks are premium even though that is what I drive now with a 55T Fontaine lowboy. I know running 2-3 trucks+ is the way to service the customer's better because many larger heavy items also have fall-off and parts loads that need to be covered as well to earn the opportunity with the customers but I just need to get started, stay conservative, cash flow positive & pay the equipment down as quickly as possible. The few guys I have seen experience solid, consistent growth have been at the 2+ truck mark but It's tough to write a financial plan for 2-3 trucks when it's going to take a solid amount of time and considerable life changes to even get truck one up and running.

 

You are exactly right, I couldnt see running a larger trailer without an established customer base. Like I said I think its wise to go with a tandem sleeper truck and a stepdeck trailer to start out.

 

It was one of the reasons why my last serious multi-year relationship ended was because she felt trucking was like a bs “something you do before a real job” where the talk was “oh yeah hes doing it for now and then later he’s going to do something better” and I knew at some point i was going to have to choose between her and the career... and I’m sorry but I enjoy it too much to go be a has-been that talks about the golden days and “how cool i used to be” So I already understand the sacrifice, i am just trying to get setup so I can do it the right way.