We are hoping to close in the next two weeks on a property that we know will *maybe* break even and more likely lose about $2K in the first year, but we're okay with that because we're getting something that we absolutely love and hope to enjoy for years to come.

Hello Doug, I am not a real estate attorney nor is this legal advice.Unless someone's state has specific laws banning contract assignments you should be fine doing the following.  

It's close to home.

Since the previous owner is getting most of the proceeds does the closing attorney issue him a 1099S and then issue my company one for a much lower amount?

Now you schedule your purchasing closing assuming the balance on the mortgage is equal to or less then the as-is value. - NOW the seller has to be willing and able to move out before your closing date.  

@Mitch Davidson I purchased a property recently and closing in May.

It is legal and very lucrative in some parts of the US. 

In terms of other factors, I'm not sure there's a lot because I did have some people express interest in filling out an application before, and I actually got really close with one potential tenant, but it was because of the alcohol policy that he ultimately decided to back out.

Each of your sales will need to have overlapping time frames (45 days to identify and 180 to close).

the other reason wholesalers wont get licensed is the guru's tell them they don't need it and its legal in very state ( which it is not) and the reasons you don't want a license are as I mentioned the fiduciary laws..