A few more pieces before you get started - but it is feasible!

Make sure to have a least 1 million in liability, loss of rents, water damage coverage, vacancy coverage, replacement cost if possible, and an affordable deductible.

Short term rentals have been around a long time and for people with smaller portfolios, it usually makes more sense to get the right personal policy that permits short term rentals, especially for a condo because there are coverages like loss assessment coverage that is needed to dovetail your coverage with the associations policy.  

However, if the rental property goes from showing a profit as it does now to generate a net loss due to the interest deduction, your losses may be limited to passive losses. 

- What is your most memorable loss or hardest lesson you had to learn?

I would look at your portfolio and see if you have anything to tax loss harvest. 

By locking in our funding, we can eliminate one source of potential distress and we can also 'fix' one of our major expenses by locking in the financing rate Increase your cash position – there will be opportunities to buy distressed assets from people who were not prepared, but you will need cash Reduce Leverage – leverage can be used to provide higher cash on cash returns however along with leverage comes greater sensitivity to any loss of income.

If you work hard for it and it goes down you lose time and money.But that depends on the risk profile you have for that money.Look at the Delta between your options and asses your risk of loss against it.

Also, there are eviction costs and rent loss during the eviction. 

Cut the price and cut your losses before sinking into another loan to rent it for years and get no return.