About to graduate and have a job offer, have little red flags. Looking for opions

We have talked some about benifits but not gotten into details. He also said he has milage, saftey, and maintanence bonuses which we would go over when i got there. I was planning on working with him a while and then once I decided it is where I want to be, then and only then move the family out. The good thing about my father living out there is on a slow week i could work for him for some extra cash. Joe did say he may have a week or two out of the year we will slow down due to weather, but normally his guys are always on the move. Hometime is dependant on the runs but he trys to use the 34 hour restart rule to coincide with hometime. Also he has 6 trucks and two more on the way. He mainly works with the energy field. His biggest account is with the oil companies delivering the oil rigs around the midwest but has some jobs with smaller windmills and such. As far as 1099 or w-2. That is a VERY good question, I didn't think to ask, thank you. I have a mechanic background so checking the trucks out should be simple enough. I know I will not use a truck that is unsafe. I had to watch as a fellow Marine was killed, literally had his head crushed, due to an unsafe truck. I won't go thru that again (still have nightmares of it). Thanks for all the info. I tried google but couldn't find much as he doesn't have a website.

 

He hasn't officially hired me. Itbis a conditional agreement. I have to pass and all that, and my background checks all have to comeback clean. He already has my mvr as i sent it to him and his insurance company. Once the cdl and certificate is in hand the final decision will be made. Right now i'm on of the two top drivers in class. And THE top student when it comes to the tests (not a single missed question so far). Oh and it isn't a contracted position. The schooling was done thru the VA so i can go anywhere. but I like his setup.

 

it started as us talking about it and he said he would check in with me during school. At first it was simply "i need drivers" then as school went on and i was doing good, mvr came back good and whatnot we talked details about the runs, the trucks, etc. At this point I just need to get the cdl in hand and wait on his insurance company to run their checks. He is using my miltary does driving to count for 2 years experience which he (and his ins) requires of his drivers.

 

Correct they were vans. I don't expect to just hop in a truck and own the road. Neither does he. But we both agree thst i should be able to drive highway from a to b. We will do a test run before hand to make sure i know what he expects me to prior. It's unconvential but it is what it is. I know the techniques needed, so I think it will just be a matter of adapting them.