If you plan to Scale. 

It is very challenging to get your AirBnB license unless you are renting out YOUR UNIT or you do 25% of your units if you have over 6 units or something along these lines.The only way I'd advise STRs in Chicago would be if you are going operate a business to scale and had the resources/local knowledge to do so.I'd actually highly suggest Michigan because there is WAY LESS restrictions.

And if the house isn't currently selling at the price you've set... that means the appraisal may come in lower too. 1 - Doesn't matter much at this scale of the business.

There is much better scale to learning from people than small advancements on a computer.

Likely going to start with private equity from family/friends but exploring other financing options to quickly scale once I get going.Thank you in advance!

On scale, you need to let go and have underlying contractual rules that bail you out in the event of fraud, incompetence, poor work, time issues, etc.

If it goes well and you can stomach it, then scale up.

Watch out for hidden costs....you still have to "develop"(Utilites, tree removal, driveways, walkways, landscaping, fencing, grading, filing, digging, hookups, ect ect.) the lot before they can place the modular.

This means to focus your time in the areas that have the greatest value & impact such as how to scale your portfolio vs working in the weeds on things like property management, repairs, rent collection, etc. 

Cheap box builder grade trash they are building now is about 250 to 275 a foot.