I would prioritize finding an accountant who specializes in real estate taxation over one that is local.There are 20+ accountants on this message board who specialize in real estate taxation.

agreeing that regulation is needed - and a mention of a state rep who has filed for more regulation and TAXATION of short term rentals. 

However,  a quarter mile North or South and the blocks start to look like a C or D.

Curious on this as well, and looking for other threads that might touch on this topic..I have an existing LLC that I plan to change taxation to C-Corp and use it specifically for property management and operating rents/expenses..

With a new tenants you lay down guidelines and make it clear you will be making quarterly inspections.

I browsed several posts about taxation on out of state LLC's set-upsin CA, but didn'tt find the exact answer I was looking for...Can someone shed some insight?

Hi Paul, definitely a question for your cross-border tax advisor as with Canadians there are implications to double taxation.

One that provides monthly or quarterly check inns as well via email.

Paid yearly. https://webapps1.chicago.gov/c...There is also a lot of city-specific info on Airbnb's own website, including the local, state, and county taxation laws for Chicago https://www.airbnb.com/help/ar...Hope this helps!

This is a re-post, but if you haven't seen it, I hope it helps: As it relates to asset protection strategies, think of the work you do with a legal adviser who, upon considering factors such as net worth, estate planning issues and taxation will offer advice regarding entity and ownership issues.