If there is a ruling in favor of the landlord they can apply for a red tag and setout with the bailiff.

For anyone that is starting out in Calgary, here is a mapping tool that I use to check land use zoning and property assessment values: https://maps.calgary.ca/MyProperty/ While analyzing one deal, I noticed that some properties have a dotted red line around it.

Attention to detail is of utmost importance in this business, and assigning income to property you don't own or not substantiating basis for a disposition (or depreciation) is a red flag to me. 

Any turnkey company (or really any company) that tries to sell you on the idea that they're doing you a favor, losing money, by 'letting you' get such a great deal, is lying - that's a used car salesman tactic and huge red flag.

I know how quickly things can go into the red in this business.

So, from the get~go as a full rental, I'm $400.00 bucks in the red, monthly.

I learned in deep red states that lawyers are usually not needed which can make the return even better.

What if one day the home owners association decided to not allow short term renting or possibly the state of HI passes laws banning short term renting (it's very controversial over here) and over night I go from a great cash flow rental to a rental thats in the red and possibly underwater if the bubble did pop.

I understand that trying to do this several time will raise red flags for the lenders, but what if once or twice only before going in with more cash?

As an architect myself, clearing the red tape and getting through the municipality review process to attain permits and then the contractor complying with the necessary inspections can be time consuming.