For my units, I usually look for someone with annual income 40x the monthly rent so I know they are financially secure. 

Wealth Building: Paying off the first STR focuses on cash flow and financial security, while buying another property focuses on scaling and wealth building.

Even if I were to rent it out on Airbnb, the cash-on-cash return isn't very attractive.Specifically, I’m concerned about:High mortgage payments and the financial strain it could cause if the property doesn't generate sufficient cash flow.Cash-on-cash return is low, even with high-revenue short-term rentals.My Questions:Risk Mitigation:Any strategies I can use to mitigate the risks associated with owning a high-value property with a large mortgage?

Many of our competitors would have walked away, leaving us with the upper hand.If you have the right mindset and the right resources, properties that others shy away from can become some of your best deals.Have you ever dealt with a property that took months to resolve?

I'm not sure if that would bring in enough money but it would certainly make things easier financially speaking while you built up your real estate portfolio. 

Always happy to connect, share resources, or do what I can to help.

I believe such plans are offered by specialty divisions of the mainstream financial services providers like CIBC & RBC.

Bigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

You can call it lazy, but perhaps also they don't have the resources to take on the potential number of small cases like this.

Bigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.