It all depends in what state your in. The easiest states to get your Dealer license are New Jersey and New York. Here's why. In order to get a dealer license their are four things that are mandatory. You have to get bonded (up to $60,000 cash or property), pass a criminal background check, credit check, and get your lot insurance. There a lot of other stuff but they all vary from state to state. The reason why NY and NJ are the easiest, is because you only gotta put up $10,000 for the bond and there is no credit check. I had a few dealers tell me they are even lenient on the background checks too. So it all depends on what state your. But I can tell you what stops a lot of people is that credit check. Some states require you to have A plus credit.
I've been out of the biz for a minute so some of the laws may have changed. But I can tell you this. The easiest way to get a license is to go in with 3 or 4 people and form a LLC or LLP. This way you split all the start up cost, and all the bills in the future. So if you got a $2000 monthly lease, and $2000 monthly insurance, you don't have to carry all that debt by your self. Plus you don't have to hire any employees to do paperwork, salesman, drivers, etc. All the owners would do that stuff. This cuts off most of your overhead, which allows you to lower the prices of your cars and compete with out dealers.
What state are you in? I can check and tell you how to get started