I know its pretty common in short term rentals, but I'm not sure about the legal implications. 

Considering the building is still legally set up as condos and they are rented at much above market rates, I'm wondering if I could still demand $1.4 million for it?

But you can use other lease option strategies, such as the cooperative assignment.As for Wisconsin and lease options, from a legal perspective they are a viable strategy. 

 I certainly expect to pay for legal advice!  

@Tom Server most states only require a separate account for ALL security deposits one holds.Of course, this is NOT legal advice and check with a competent attorney.

My wife and I previously owned real estate in our joint names in both Florida (where we currently reside) and in Virginia (where we previously reside)Following ur research and some legal advice, we established two trusts (one in each of our names) and also two LLCs one for all the properties in Virginia and the other for all the properties in Florida.We have deeded all the properties in Florida into the Florida LLC, but we have not done so yet for the Virginia LLC.

There are definitely lenders out there who are not charging interest in the traditional sense.

I know that renting up your investment can be one of the most confusing and nerve-wracking parts of the process (especially in a place with as much bureaucracy and legal hurdles as Chicago) and am more than happy to talk with anyone about that.

if you can house hack, house hack.good luckHi Nickolas,That is definitely solid advice and I definitely see your point.

If so perhaps the state requires you to have a local “registered agent” for purposes of receiving legal notices.