Hi Ricky,Being in operation for 10 years with mid seven figures of assets and NNN leases,it would be wise to speak with your tax advisor regarding if the tax set up should be an LLC, an S-Corp  or a C-Corp.It would also be wise to speak with an asset protection attorney to find out if this is something that might be beneficial to you in that area.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

I’m a long term rental guy, so make less than an Airbnb type operation on cash-flow .  

Im a medium sized operator - 46 units- and my typical deal has an ARV from 200 to 230 when its finished.

By year three, I aim to cover all operating costs and, by year four, to generate positive cash flow.Experienced investors say it’s crucial to persevere through the initial challenges while gradually building credibility through positive reviews, and I believe them.

If you would really like to explore the sector : why not go and message 10 to 20 operators and offer to look after their property or clean their property for a month in exchange for their knowledge and details on the numbers.

Assuming a 40% expense ratio, the net operating income at the current income level would be around $19,440 annually and $28,800 after renovations.At a $360,000 asking price, the cap rate based on current NOI would be 5.4%, which is low for a park with park-owned homes and required renovations.

This could include new appliances, energy-efficient windows, or custom finishes.Clean and Declutter: Ensure the property is clean and free of clutter.

You could form an LLC and have the operating agreement that allows your boss to require you to purchase his membership interest (or allow you to purchase his) in a given time frame.

Most people don't know how to use a wood burning fireplace correctly - operating the damper, not closing the damper until the fire is completely out, going to sleep with the fire or coals still burning.