And being in the position of owner, we can either drastically help or hinder the people who are living there.

And being in the position of owner, we can either drastically help or hinder the people who are living there.

An LLC can actually hinder you when starting out, as conventional lenders will almost never lend to an LLC.

What markets in the IL, chicago, or nearby Lake Michigan areas are best for creating new STRs without being hindered by zoning regs?

If you are stuck with a low fee contract for a long period of time that can be a negative especially if it hinders redevelopment and site layout of the land.This property doesn't sound that great from what you are initially saying.

So, for me personally, I would love to add a property that would only be a vacation rental and where there are no potential hinderances an conflicts with a long term rental shortage. 

If many listings have blocked dates, it will prevent the site's algorithm from accurately matching a user's search criteria to the most relevant listings, leading to a poor user experience and potentially lower search engine ranking.In conclusion, blocking dates on Airbnb can have a significant impact on the Airbnb algorithm by decreasing the amount of available content, negatively impacting the user experience, and potentially hindering the site's algorithm from accurately matching listings to user searches.

if this is non-owner occupied you likely will be limited to 75% LTV (maybe even 70% LTV) which will hinder the "Take the equity you gained ..." part of this good plan.Note after you have extracted the equity, you can turn it into rental or continue living there. 

If the market appreciates you still do not fully realize the appreciation because the value of the property is hindered by being rent controlled.So better off to look elsewhere.BTW I think rent control does no one any favors. 

Now moving on to my concern, that is hindering me at the moment.