Am I being underpaid?

I think 1500$ per week is not bad, even on 1099 form. If you like the company, if you are feeling comfortable with their truck/trailers, stay with them. Lots of OTR companies does not have work right now..

 

See what Craiglist have Worth cheeking..

FedEx Ground contractor looking for full-time CDL class "A" local driver with Double/Triple endorsement in Grayslakeg, IL.

Starting from 04:00 PM (16:00h) to approximately 00:30 AM (12:30h), Monday through Friday night, weekend home. Job consists of making steady(same) short line haul runs between FedEx Ground locals terminals in Chicago area every night, hook and drop.

DRIVER REQUIREMENTS:

-Applicant must have 1 year verifiable CDL class "A" experience.
-Applicant must have doubles endorsement before applying for job.
-Clean driving record with no major violations in the past 3 years.

 

That guy has had that ad running for at least three years.

 

Your accountant is stupid, get another one.