Quote from @John Warren: @Delroy Watson I would check to see if you can do this the "right" way and make it an ADU.

Be sure to check out the free tools BP provides to help analyze deals you may have and also market insights.

We simply include the tax on the invoice sent to guests, which makes it easier to track and ensures we're covered for tax purposes at the end of the year.For Chicago, I’d recommend checking directly with the city’s tax office or a CPA, but generally, you’ll need to register with the city, collect the hotel tax from guests, and remit it on a regular schedule (likely monthly or quarterly).

Whether it applies or not it's always a good idea to check with a professional first so thanks for the reply.

I spent many years managing myself and personally collecting rent checks. 

I would find a Realtor there who is an Investor themselves so they can help you identify properties that will work as an investment, not as a commission check for themselves.

Thank you Preston I will check it out. 

My recommendation would be to drive down there on a weekend and just check out the places you like and see the city before you dive in.

The right agent will have worked with Canadians before, will have lenders set up that can work with Canadians and will have a seamless process for management.Not only can an agent set you up with a GC, property manager, lawyer, insurance broker, inspector and everything else you need, they can analyze deals and put numbers in front of you.Your job as an investor is to vet the vendors they are providing and double check their analysis.  

just double checked my lender is now 80% LTV for short term rentals only 85% for long term rentals