@Skye Fleming....WHEW!! You asked some questions with no short answers and most with different answers depending on who you ask. 1) Probably the biggest and perhaps only benefit is that what you cannot wholesale can be a possible referral for an agent...2) It's not on the IL books as being illegal as it in some states but some view it as such so some suggest having your own real estate broker license to avoid legal issues. 3) No certain contract. A good lawyer that works with investors can draw you up a simple one that can protect you. 4) I've know people to do it but it's not something to be done without a lawyer and without being extremely clear about what it actually entails on your part and the part of the seller. 5) Unfortunately, nothing simple about it as some might think, my suggestion is to always to CYB and always, always, always have an attorney...6) Define "enough" money. Creatively, you can have enough money to do just about anything you want in real estate. It's more of a define what you want to do first, then decide what you actually need in order to get it done. Sometimes, it's not the money that's stopping you, but the creative way to get it done that's more of the issue.