Non-traditional driving job

Another company won't be ok with it, so don't tell them.
You're former military, so doubt you'll cower in a corner sweating crap like that..

 

1st and foremost, thank you for your service. Many retired military personnel go into trucking. Problem is, they are usually horrified at the lack of discipline they are used to. What you are describing, sounds like you'd like to be a "casual" driver, maybe a couple "casual" jobs to make it work. Too bad trucking doesn't work that way, like say a free lance website creator. I'd have to think the logistics of several jobs would be maddening, and not too popular with any of the bosses. They almost feel like they own you, how dare you drive for someone else? Regardless of what some may say, tanker job is the best gig in the business, and drivers try their whole career to get a job like that. I say, stay put, show the boss you can do a good job, they'll take it from there. For the record, most gas tanker jobs are at night, and you don't want to drive an atomic bomb in todays daily traffic. Night time the right time,,,for tankers.

 

No, it doesn’t sound practical.

You want your side gig to pay more than your main gig. If the side gig is going to pay SIGNIFICANTLY more (your words), why would that be your side gig? A temp company isn’t going to pay significantly more than your main gig. If it does, the problem is your main gig. Replace it first.