Are our plan realistic?

IDK, sounds like a good plan. With your Dad taking care of many of the details of the loads and being around to help, I think you'll be able to pull it off fairly well.
If you have the resources to get your CDL without having to fork over bucks to a school and go through some company's training regime, you're ahead of the game.
I'd say go for it myself!!

 

Do it before the law changes in February. Much tighter restrictions on how you can obtain your CDL.

 

Three weeks and Yes.

I got a CDL in three weeks. With personalized instruction, a road legal truck and no distractions from the other students I could of done it in 2. Even if you went to a company or private school your first job would involve driving with a trainer for the first month or so anyway.

The only hitch I see is insurance. With no 160-hour training certificate and zero miles experience in a CMV it's going to cost a fortune to insure you. Still, if you can find a company willing to insure you with a little luck you could probably squirrel away $20k in three months

 

Waiting for covid restrictions is all well and good but you better get your CDL and get some training with your dad in the mean time. Way things are going you could be a long time waiting in the wings.
Your dad could probably use the extra eyes and ears for the first couple weeks too.
Man up, go get that money.

 

Just one thing, you most certainly will start hating each other after doing business together and doing team driving.