Doing this (renting both entire house and single bedroom rental) allows us to be able to tap into 2 separate target audiences and accomodate those singer travelers, couples coming to the area that would normally scroll past our listing due to size/cost. 

. - You've got some pretty solid information above and concurrence that it shouldn't cost nearly as much as you thought, but on a separate note, I'd like to understand your situation a bit better.You are currently just looking for a Chicago property to purchase and asking the quit claim question in preparation for closing? 

It may be more helpful to put some of your specific questions right in a post or separate posts.

Separate the work into 3 separate categories: 1) Those that are specifically related to the future STR usage, 2) Those that benefit you while living in the house and have zero bearing on the future STR, 3) those that benefit both you and the future STR....assign a percentage to the usage.Be specific and complete.

This won't change the numbers at all, but it will correctly reflect the personal ownership of the RV.Since the RV is in our personal name, and our two LLCs use it for travel, should we treat the RV as a separate rental business (sole proprietor) and rent the RV out to our LLCs when needed for travel?

My wife has been handling all the complaints that we are filing with the DA, etc.If nothing else we should all band together and file separate complaints to whoever may help us. 

Let me add some new wisdom to this.Try not to see social media as "just another channel to try my luck".It is not a separate thing, especially doing SEO or paying for ads.When it comes to lead generation, it is not (just) about generating that lead.

Look for properties with low taxes, separate utilities, strong demand, and potential for rent increases.

I am a rental property investor but i hate making things complex and the last thing i wanted to do was create a separate bank account for each property..yikes.

We have a few properties that are held as JV's in separate LLC's and just want to make sure all is above board.Thank you, and Happy Holidays!