You could then utilize bonus depreciation for the equipment to increase your deductions which would help offset the capital gains.Both strategies can be complex, so always be sure to discuss these with your tax professional.Have you utilized either of these strategies?

For me, the extra $20K/yr still wasn't worth being covered for a rare event like that.

This article lists the areas had the highest percentage increase in the past five years. https://fox8.com/news/these-cleveland-area-cities-have-the-f...

It increases your income and protects you from the risk.

Sure a SFR by itself is worth x but this house is not by itself.

In a market where it is increasingly difficult to buy real estate, where expenses are going up, and rents are trending flat or downward, what drives you to keep investing in income properties?

There has been under construction in this space since GFC in 2008-09, so now big lack of supply, and we have multiple offers on spaces and able to increase rental rates 10-11% on new leases, plus we write in CPI step-ups to hedge inflation. 

At $250/night (This is mostly a guess as to value of a VIP room) with 28 nights it would be 42.8 years to break even without accounting for inflation (today's dollars are worth more than tomorrow's dollars).Do you get any of the return from the room being rented out on the days other than the 28 days? 

And in any 1031 exchange, you only get full tax deferral if what you buy is worth at least as much as what you sell. 

The art is in making sure the 1:50 that win's, is worth it all.