Hello Brandon,
I do not consider myself a wholesaler (although it is a minor part of my real estate strategy). My advice would be to get in contact with a reputable local attorney who can guide you through how assignments and double closings work. Also, consider joining your local REIA for mentorship and guidance from investors who are used to working in your area.
Wholesaling has become a heavily saturated field. Everyone and their sister thinks that they can wholesale thanks to the proliferation of real estate gurus promulgating this approach. There are certainly possibilities to be successful in this area, but these days it is larger wholesalers with people and systems in place who seem to be having the most success. Everyone else is left fighting for scraps, especially in big city markets. It is not something I am interested in anymore, except in some specific circumstances.
Then there is Wisconsin Real Estate Law. WI Stat § 452.03 (2018) states:
Except as provided in s. 452.137, no person may engage in or follow the business or occupation of, or advertise or hold himself or herself out as, or act temporarily or otherwise as a broker or salesperson without a license issued under this chapter. The board may grant a license only to a person who is competent to transact that business or occupation in a manner that safeguards the interests of the public, and only after satisfactory proof of the person's competence has been presented to the board.
Then you have this regulation:
WI Stat § 452.01 (2018)
(2) “Broker" means any person not excluded by sub. (3), who does any of the following:
(a) For another person, and for commission, money, or other thing of value, negotiates or offers or attempts to negotiate, whether directly or indirectly, a sale, exchange, purchase, or rental of, or the granting or acceptance of an option to sell, exchange, purchase, or rent, an interest or estate in real estate, a time share, or a business or its goodwill, inventory, or fixtures, whether or not the business includes real property.
(b) Is engaged wholly or in part in the business of selling or exchanging interests or estates in real estate or businesses, including businesses' goodwill, inventory, or fixtures, whether or not the business includes real property, to the extent that a pattern of sales or exchanges is established, whether or not the person owns the real estate or businesses. Five sales or exchanges in one year or 10 sales or exchanges in 5 years is presumptive evidence of a pattern of sales or exchanges.
This is an absolute death clause, if you ask me. Since it precludes you from making more than 10 sales in a five year period, even on property where you have an interest. But perhaps a local attorney could guide you through this regulation in more depth. It would seem that attorneys also have leeway to make real estate transactions under WI law, so they are a good place to start your discussions about wholesaling if you are trying to do it right.
You can also wholesale out of state, but keep in mind that each state also has its own rules and regulations as well. Wisconsin seems to have some of the easier real estate licensing education requirements, so it may be worth it to just go that route and wholesale 'legally'.