A little more entry but so flexible for accounting.

Depending where your rental is in Chicago, you should also be flexible with your requirements.

Since you're selling the business and real estate to a partner/friend you will have some flexibility in value determination. 

Staying Flexible in NegotiationsAs agents, licensees are bound by ethical and legal rules that may limit how they negotiate or market deals.

That is something that is growing due to the limitations of STR.MTR is something that will help you but you will have to be a bit flexible in the times that you are planning to come in.Management is cheaper than STR, but you have to consider other factors such as close to places where those MTR are in need.

You have full flexibility to use none, some, or all of the rehab budget.If you have any questions, I’d be happy to discuss how we structure our loans to best fit each client’s needs.

LLC's separate your personal assets from your investments and offer you protection from lawsuits related to your property, they can help to establish a more professional image if you plan to expand, and they provide some flexibility on how you are taxed.There are some drawbacks, included fees and administrative work, but it's ultimately best to consider speaking with a CPA to determine the best option for you. 

As I'd imagined, it seems like there are no hard-and-fast ways that a deal must be structured, but rather there is room for flexibility depending on the situation, and in any case consultation with experienced professionals at every level is key.

Find one that can be custom to your needs, has flexible pricing, no long-term, high-cost memberships and excellent customer services to determine how to best market to your leads.

It's hard to beat the flexibility of Podio, although it does require some time & effort to set it up.