buying and selling cars through dealer?

ive made a deal with this dealer it sounds legit just wanted to see if anyone ran into this before. ill be going to dealer auctions with hiim and buying 1 or 2 cars and paying him 300 dollars for each car i buy. im going to then get titles in my name through the state and sell them for profit. will this work i know i can only sell 5 of them a year after five i was going to have my brother put 5 in his name then my sister and then my gf so thats 20 a year which i doubt i will do prolly around 10 or 15. is this a stupid plan or does this sound like it will work and can i really get cars very cheap a dealer auctions the dealer is telling me that im going to be abel to. let me know any dealers out there. its in the state of maryland.