How much of a pain will it be to manage tenants?

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If you’re not using a 1031 exchange, you’ll need to account for this.Reinvestment Risk: Entering new markets and managing multiple properties may present challenges, especially if you’re unfamiliar with the areas.Alternative StrategiesBefore committing to selling, consider these options:Leverage the Equity (HELOC or Cash-Out Refinance):With a 3.1% loan, selling might not be the best first move.

So now an employer has the affordability to afford the coach/teacher manager and the over-sized staffing.

However, consider STR seasonality, local regulations, and management demands, and ensure your equity loan and new primary residence costs fit comfortably within your budget.

Self-purchased and managed.

They both own thier own management companies as well, so they understand the needs for investors when it comes to insurance.Best,Brad 

If not ask to speak with a manager.

How would you manage risk? 

You will learn the time and effort required of managing such a unit.