Sometimes, a commercial policy (businessowners or package) is used but generally that is more expensive. 

Might require prospective tenant to carry renters insurance.

Analyzing properties is a challenge, hoping you don't forget to add something to the expenses! 

This is because I do not require the cash flow to live or make my payments.  

So I put a bunch of my expenses there, and put equivalent amount in CD for a year - basically doing rate arbitrage.

Workarounds:- Not all assumable mortgages with be at such a low LTV (loan to value) there are examples of properties that require 15-20-30% down.

I have reached out to the city to see what would be the requirements.

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

This can involve public hearings and meeting specific requirements.Surveyor: Hire a surveyor to map the property and define the boundaries of each condo unit.Legal Counsel: Work with a real estate attorney to ensure all legal requirements are met and the condo conversion is properly documented.Financial and Operational Considerations:Condo Fees: Determine the monthly condo fees for maintenance, repairs, and other communal expenses.Insurance: Ensure proper insurance coverage for the condo association and individual units.Reserve Fund: Establish a reserve fund for future repairs and maintenance.Tax Considerations:Initial Purchase with 1031 Exchange: 1031 Exchange Basics: By using a 1031 exchange, you defer capital gains taxes on the sale of your previous property by reinvesting the proceeds into a new like-kind property.Down Payment and Financing: You're putting down $220,000 and financing the remainder at 8% over 20 years, resulting in a monthly payment of $2,593.Converting to Condos and Selling Units:Capital Gains Deferral: The 1031 exchange allows you to defer capital gains on the initial exchange.

If that is the case, many lenders will require for you to have some skin in the game.