Dipping my toes in…

Yes

 

Get a job in the trucking sector you're looking to get into for at least some amount of time before taking the plunge.

 

Your current gig runs 3 months on, 3 months off. It will take you at least a week to get the truck back to work, and you'll need to stop the truck at least a week before you ship out. Realistically you're looking at running the truck at most 1/3 of the year, and not necessarily during the most profitable seasons.

Secondly, trucks are designed to be run, not sat in the yard so your maintenance costs are likely to be higher. Along with that you need someplace to park the truck. A dump truck sitting in an unsecured lot for 4 weeks isn't going to be there on week 5.

Third, unless you've done dump work previously, you're trying to start a businesses in an industry you don't know. I spend a lot of time in bars, and understand the basic mechanics of running a successful bar. That doesn't mean it's a good idea for me to start a bar and continue to try and work my current full time gig.

 

Simple answer. Trucking isn't a part time job.

 

Do you know somebody on the inside?

If not, I think that you will have trouble getting loads because the pits, brokers, and construction companies are going to expect you (and your equipment) to be ready when they call. With your limited availability you will probably be very low on their list, if they're even willing to put you on the list in the first place.

This will be compounded by the fact that you're brand new to trucking and have not already established a name for yourself.

 

Actually let me expand on my comment. O/o isn't a part time job. You could work for a temporary agency.