Probably legal, but complicated and asking for trouble.

It is a complicated loan, but the average Seller and listing agent don't know that, which is why it is important to have a conversation with the Buyer's Agent and loan officer on the process to get it streamlined as best as possible.  

Then, be honest and open about it, with messaging that flows from the deep truth of why you are a wholesaler.To not disclose this complicates things down the line. 

If you are going to set it up as a syndication structure where someone is charging fees/equity for doing all the work then you will need to work with a syndication attorney to set it up and the structure gets a little more complicated. 

@Cari Childers It makes it more complicated to borrow from banks with an LLC.

I've never transacted with a wholesaler before, how much does that complicate the process? 

I am studying for my license currently in the hope's of getting into investing and also chicago has the law were u can't buy more than one property at a time without having a realestate license.Sounds like you have a complicated situation that is going to take a bit of time to work through.

This is going to be even further complicated by you having a property on the east side of Cleveland.

In most cases, neither is warranted.Warning: I am not an attorney and this can be a complicated topic.

The only thing that complicates everything is that the house is attached to another house that we don't own (we are in talks with that homeowner to make sure everything goes smooth), and it is two different insurance companies.I'm really posting on behalf of my dad, this is his first time owning a home and he still lives up in NY. thanks