Say a high school senior wants to go to his dream college, but the cost are expensive and he can’t go (at the moment), so he ends up going to his last choice for a lower price. Now after he finished his sophomore year, he decides to apply as a transfer student to his dream school to be a junior.
- would it be smarter to apply as a transfer student and get in and initially pay half the price he'd have to pay if he applied as a freshman ( all 4 years) for going 2 years ( junior & senior )?
- or would it be safer to apply as a freshman since most freshman undergrads have a higher chance of getting in anyway?
I’m not saying apply as a freshman student but really being a transfer!
I’m saying applying as a transfer ( in college )
Or applying as a freshman ( high school )
sorry confusing ik. 
This is not an either or situation.
Apply now, and see if you are admitted and what the financial aid package looks like. If you are admitted, and the aid package makes the place affordable, go.
If you are admitted, but the place is unaffordable, choose among the affordable options and go there.
If you still like the dream college a year or two from now, then apply as a transfer, and if the aid package makes it affordable you will be able to decide at that time whether or not you actually do want to transfer.
To keep from feeling like you have to go to your “last choice” because of a lower price, look around a bit more thoroughly for low-cost options, and apply to two or three of them. That way if you are admitted to more than one of the low-cost places you will have a choice come April.
It is common for students to apply for frosh admission while in 12th grade. If they are not admitted, or the financial aid is not enough, they may go to another college (possibly a low cost community college) and try again as a transfer in their second year of college.