How much experience do you think is needed before becoming an O/O?

All valid points. I've considered the worst case scenarios, and that's where I run into my gut telling me to hold off a while longer. Which is part of the reason I haven't made a move just yet.
I was stupid, financially speaking when I was in my 20's. I literally did everything that anyone with a brain would tell you NOT to do. Loaned money to relatives, co signed on a loan for a person who then filed bankruptcy, spent money like a congressman. Oh, and bought my first house and started a family.

I spent my 30's digging out of the path of destruction I'd created. Believe me, it was not easy at all. Bankruptcy was probably a better route to go than fighting tooth and nail to get out of said mess. But, I was too stubborn to admit defeat, and kept pressing on.

Now in my early 40's, I'm fortunate that I've gone through all that, and have a good idea what not to do. While I'm not swimming in money, I'm doing ok, even with the high expenses I currently have. Barring anything crazy, on my current path, my monthly expenses will be in the $2300 range in about two years. Or I could take the 40k I've set aside for a truck and end a lot of it now, and get the expenses to around $3000. But then I will have nothing for a truck, or the repairs.
My gut says to stay the course another two years, and build on the $40k I have, while chipping away at the debt I currently have. But my mind screams to make a move.

But in two years we may be worse off, economically speaking than we are now

 

If i were in your shoes i might buy a truck for maybe half the cash if i could and just start doing things to it now. But i prefer older trucks/engines and have over time built a decent amount of a mechanicing toolbox and knowledgebase. This presumes that the same is your skillset and inclination and that you could at least put it in a garage or barn on your own property though. Something i STILL cant do and severly limits what i can do

 

I've been toying with that thought as well. I have a place to put a truck inside for an extended period of time, and can do most of the mechanical stuff myself, and I have enough people around me that have the knowledge in areas I don't, mechanically speaking.

But then if I go that direction, then I'd likely be looking at older trucks (probably pre 2007 or whatever year the DPF became a thing.) Most of the places I've been interested in leasing to require like 2010 and newer. But I know there are places that take older trucks. Going all in and getting my own authority isn't in the cards at this point, for various reasons but the big one being I'd be running off the load boards to start out, and I can't justify spending money to run like that. Just too much uncertainty there for my liking.

The beauty in all this is I don't need to be in a hurry to do anything at this point. So I have time on my side to make sure I get this thing right if I do it.