For 'smaller' amounts of under $100k many will even do an automated online appraisal and employment check, instant issuance and funding in five or so days. 

Online Services for Trust Setup: Has anyone used online services for setting up a trust?

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.?

Carefully analyze if the potential rental income can support that level of financing costs and operating expenses.Get realistic projections on expected occupancy rates, average nightly rates, operating costs etc. from experienced short-term rental operators in that market.Calculate the debt service coverage ratio (DSCR) lenders will require based on the projected net operating income.

Depending on the deal's profitability, some will only require you to bring 10% + closing costs to the closing table.

This means that, while companies may "require" experience with it, they may not actually be able to find a good candidate who has that experience.

Also, the carry forward losses can be used to offset other passive income (e.g. if you currently have another rental with income or eventually have another rental property with income).Short-term rentals have different tax benefits and requirements.

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.

The larger projects I am looking at, would require more funds (probably around $500,000) and a longer hold period (3-5 years).