Business Dilema

I think he means leave the company you're with and lease on somewhere else. I understand that is your plan.
You have a truck that you know. You haven't spoken of any mechanical problems . So it seems dependable.
If you trade you may get a problem truck.
It seems you're willing to go $20k more in debt with an unfamiliar truck to buy some time.
Imo, I would keep what you've got. Remove as much weight as possible and hopefully move to a company where you can make a living.
How much is the penalty for missing a payment ??

 

He was talking about the carrier you are leased to.

 

I have to believe you can find a used truck parked somewhere. Yes, there will be some repair required. There always is with a unknown truck.

There is perhaps another avenue. Maybe your lender will allow you to make interest only payments until you can get back on your feet. Yes, you will pay more interest in the long run but you will save by not buying another truck and all the expenses that come with that.

 

You are going to be carring negative equity for a long time ..... That's never a good thing